- Iridium-catalyzed double incorporation reaction of N-benzylmaleimide to styrene via ortho-C-H bond activation, initiated by precoordination of the double bond of styrene to iridium
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Reaction of styrene with N-benzylmaleimide in the presence of [IrCl(cod)]2 (5 mol %) and bpy (10 mol %) in an autoclave (1 MPa of Ar) at 150°C for 18 h stereoselectively led to the formation of a new cyclic product. The structure of the product suggests that a novel iridium-catalyzed double incorporation reaction takes place via a metallacyclopentane formed after ortho-C-H activation.
- Kiyooka, Syun-Ichi,Takeshita, Yushi
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Read Online
- NOVEL UREA 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
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Page/Page column 31
(2020/05/29)
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- NOVEL UREA 6,7-DIHYDRO-4H-PYRAZOLO[4,3-C]PYRIDINES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
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Page/Page column 33
(2020/05/29)
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- NOVEL 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for mating the compounds.
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Page/Page column 78
(2020/05/29)
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- NOVEL INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
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Page/Page column 120
(2020/11/13)
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- NOVEL INDOLIZINE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
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Page/Page column 91
(2020/11/12)
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- NOVEL PHENYL AND PYRIDYL UREAS ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
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Page/Page column 112
(2020/11/13)
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- Preparation method of N-(aryl/heteroaryl) alkyl-diamide
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The invention relates to a preparation method of N-(aryl/heteroaryl)alkyl- diamide, which comprises the following steps: under the protection of nitrogen, sequentially adding transition metal, phosphine or nitrogen ligand, cocatalyst, alkali, solvent, Nhalogenated cyclodiamide, alkyl aromatic ring or alkyl heteroaromatic ring compound into a reaction container, carrying out oxidative amination reaction at 80-140 DEG C, and till the reaction concludes after 6-48 hours, evaporating and drying a solvent and carrying out column chromatography separation to obtain an N (aryl/heteroaryl) alkyl diamide compound. The invention is simple in synthesis process, mild in reaction condition, high in yield and easy to industrialize.
- -
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Paragraph 0052-0053
(2020/12/29)
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- Photoredox/Cobalt-Catalyzed C(sp3)-H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution
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The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp3)-H functionalization under external oxidant-free conditions is achieved. This transformation relies on the keto-enol tautomerism of 1,3 dicarbonyl moiety, i.e., the enol form of 1,3-dicarbonyl derivatives with relatively lower oxidation potential can be activated by the excited acridinium photocatalyst. The electron and proton eliminated from the substrate are immediately captured by a cobaloxime catalyst to exclusively afford a-carbonyl radical for highly substituted 10-phenanthrenols in good to excellent yields.
- Guo, Jia-Dong,Yang, Xiu-Long,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
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supporting information
p. 9627 - 9632
(2020/12/21)
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- NOVEL, HIGHLY ACTIVE PYRAZOLO-PIPERIDINE SUBSTITUTED INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
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Page/Page column 101
(2019/05/22)
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- N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N -chlorosuccinimide
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The direct chlorination of C-H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C-H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents and also heteroaromatic ones were found to be well tolerated. Both the experiments and theoretical analysis indicate that the reaction goes through a process wherein NHPI functions as a catalyst rather than as an initiator. On the other hand, the hydrogen abstraction of the C-H bond conducted by a PINO species rather than the highly reactive N-centered radicals rationalizes the high chemoselectivity of the monochlorination obtained by this protocol as the latter is reactive towards the C(sp3)-H bonds of the monochlorides. The present results could hold promise for further development of a nitroxy-radical system for the highly selective functionalization of the aliphatic and benzylic hydrocarbon C-H.
- Li, Zi-Hao,Fiser, Béla,Jiang, Biao-Lin,Li, Jian-Wei,Xu, Bao-Hua,Zhang, Suo-Jiang
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p. 3403 - 3408
(2019/04/01)
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- A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds
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Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.
- Duchemin, Nicolas,Buccafusca, Roberto,Daumas, Marc,Ferey, Vincent,Arseniyadis, Stellios
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supporting information
p. 8205 - 8210
(2019/10/16)
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- Highly Efficient Copper-Catalyzed Amidation of Benzylic Hydrocarbons Under Neutral Conditions
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A ligand free method has been developed for the amidation of benzylic hydrocarbons. A range of benzylic amides has been prepared with the use of dicumyl peroxide and a copper catalyst in good to excellent yields.
- Howard, Eva-Louise,Guzzardi, Norman,Tsanova, Viliyana G.,Stika, Angeliki,Patel, Bhaven
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supporting information
p. 794 - 797
(2018/02/21)
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- Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation
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The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.
- Song, Tao,Arseniyadis, Stellios,Cossy, Janine
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supporting information
p. 8076 - 8080
(2018/06/15)
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- Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.
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The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).
- Ni, Shengjun,El Remaily, Mahmoud Abd El Aleem Ali Ali,Franzén, Johan
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supporting information
p. 4197 - 4204
(2018/09/25)
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- Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups
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The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron-withdrawing groups, including ketones, esters, amides, imides and nitrile groups.
- Pichon, Ma?va M.,Stauffert, Fabien,Addante-Moya, Luis G.,Bodlenner, Anne,Compain, Philippe
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p. 1538 - 1545
(2018/04/20)
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- Mechanochemical N-alkylation of imides
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The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.
- Bri?, Anamarija,Dud, Mateja,Margeti?, Davor
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supporting information
p. 1745 - 1752
(2017/09/27)
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- Simple and efficient synthesis of N-alkyl and N-aryl succinimides in hot water
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A new, simple synthesis of succinimides is described. The reactions were carried out under the ultimate green conditions excluding both catalyst and organic solvent by applying simple stirring at 100 °C. A wide variety of N-susbstituted succinimides have been prepared in high yields by using succinic acid and primary amines in hot water. Yield of N-alkyl substituted succinimides were found to be higher than those of N-aryl substituted succinimides.
- Bozdo?an, Burcu,Er?at?r, Mehmet,Demirkol, Onur,Akba?lar, Dilek,Giray, E. Sultan
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p. 217 - 223
(2017/01/22)
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- Synthesis of Cyclic Imides by Acceptorless Dehydrogenative Coupling of Diols and Amines Catalyzed by a Manganese Pincer Complex
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The first example of base-metal-catalyzed dehydrogenative coupling of diols and amines to form cyclic imides is reported. The reaction is catalyzed by a pincer complex of the earth abundant manganese and forms hydrogen gas as the sole byproduct, making the overall process atom economical and environmentally benign.
- Espinosa-Jalapa, Noel Angel,Kumar, Amit,Leitus, Gregory,Diskin-Posner, Yael,Milstein, David
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supporting information
p. 11722 - 11725
(2017/09/07)
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- MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS
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The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.
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Paragraph 00394
(2017/09/05)
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- Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst
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In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.
- Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Shimizu, Ken-Ichi
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p. 891 - 894
(2016/03/15)
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- Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita
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Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.
- Eloh, Kodjo,Demurtas, Monica,Mura, Manuel Giacomo,Deplano, Alessandro,Onnis, Valentina,Sasanelli, Nicola,Maxia, Andrea,Caboni, Pierluigi
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p. 4876 - 4881
(2016/07/06)
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- An Efficient One-Pot Synthesis of Bis Butenolides
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3,3′,4,4′-Tetramethyl-5,5′-dioxo-2,2′-bifuran-2,2′(5H,5′H) diyl diacetate was obtained from the reaction between 2,3-dimethyl maleic anhydride and acetic anhydride in the presence of zinc in toluene. This easy synthetic route gave bis butenolide in excellent yield.
- Bayat, Mohammad,Fox, Joseph M.
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p. 1661 - 1664
(2016/09/23)
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- Preparation method of benzylamine compound
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The invention discloses a preparation method of a benzylamine compound. The method adopting an aryl methane compound as a raw material comprises the following steps: carrying out an NBS bromination reaction to synthesize a bromobenzyl compound, carrying out an N-hydrocarbylation reaction to synthesize a 1-benzylpyrrolidyl-2,5-dione compound, and carrying out a hydrolyzing reaction to obtain the benzylamine compound. The preparation method of the benzylamine compound has the advantages of wide source of the raw material, no need of separation of intermediates generated in above reactions, realization of an all-in-a-pot technology, simple operation, mild reaction conditions, high reaction yield, few three wastes, and convenience for industrial production.
- -
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Paragraph 0038-0040
(2017/01/23)
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- Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N -alkylation of heterocyclic compounds
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Various ionic liquids (ILs) were screened for their phase-transfer catalytic (PTC) activity using the N-alkylation of nitrogen heterocycles as the model reaction. Immobilized ILs behaved extremely well and proved to be far better catalysts than conventional homogeneous PTCs in terms of their stability, easy recovery, and reusability. The investigation also demonstrated that quaternary tetraalkylammonium salts offer very high catalytic activity, whereas aromatic heterocyclic tetravalent nitrogen catalysts (imidazolium- and pyridinium-based salts) were poorly active.
- Dogra, Shallu,Sharma, Madan L.,Singh, Jasvinder
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p. 945 - 953
(2015/09/28)
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- Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes
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An efficient copper-catalyzed amidation of benzylic hydrocarbons and inactive aliphatic alkanes with simple amides was developed. The protocol proceeded smoothly without any ligand, and a wide range of N-alkylated aromatic and aliphatic amides, sulfonamides, and imides were synthesized in good yields.
- Zeng, Hui-Ting,Huang, Jing-Mei
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supporting information
p. 4276 - 4279
(2015/09/15)
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- Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
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Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
- Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
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p. 1008 - 1016
(2015/08/18)
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- Palladium-catalyzed C - O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones
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5-R-Pyrrolidin-2-ones were synthesized by Pd/Sibunit-catalyzed C - O hydrogenolysis of 5-R-5-hydroxypyrrolidin-2-ones with molecular hydrogen.
- Turova,Berezhnaya,Starodubtseva,Ferapontov,Vinogradov
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p. 859 - 863
(2015/12/24)
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- Metal-free C-N cross-coupling of electrophilic compounds and N-haloimides
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When DBU is added, the cross-coupling reaction between alkyl halides (halogen = Cl, Br and I) and N-haloimides (halogen = Cl, Br) occurs, resulting in the formation of aminated products. A halogen bond activated nucleophilic substitution mechanism was proposed. The methodology represents an elegant example of applying the halogen bond activation strategy in an organic transformation.
- Zhang, Luyan,Li, Yanru,Jin, Long-Yi,Liang, Fushun
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p. 65600 - 65603
(2015/08/18)
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- Colloid and nano-sized catalysts in organic synthesis: X. Synthesis of carboxamides by direct amidation of carboxylic acids and transamidation catalyzed by colloid copper
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Abstract It was found that in the presence of colloid copper the direct amidation of some carboxylic acids with primary and secondary amines in benzene with azeotropic distillation of water became possible. The catalyst was proven to be suitable also for transamidation reaction of a number of carboxylic acid amides under mild conditions in solvent-free conditions.
- Mokhov,Popov, Yu. V.,Budko
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p. 820 - 826
(2015/06/08)
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- Zinc-catalyzed selective reduction of cyclic imides with hydrosilanes: Synthesis of ω-hydroxylactams
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Cyclic imides were selectively reduced to the corresponding ω-hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2 2H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.
- Ding, Guangni,Lu, Bin,Li, Yuyuan,Wan, Jun,Zhang, Zhaoguo,Xie, Xiaomin
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supporting information
p. 1013 - 1021
(2015/03/30)
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- Method for preparation of amide and imide from alcohol and nitrogen Containing Compound
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The present invention relates to a method for preparing amide and imide from alcohol and a nitrogen containing compound and, more specifically, to a method for preparing amide and imide by using: a catalytic composition obtained by reacting a mixture of a transition metal complex and an N-heterocyclic carbene precursor with base or by reacting an N-heterocyclic carbene precursor with a mixture of a transition metal complex and base; or a transition metal complex catalyst including an N-heterocyclic carbene.
- -
-
Paragraph 0200-0204
(2016/12/07)
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- Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction
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The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.
- Maity, Arnab Kumar,Roy, Sujit
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p. 2627 - 2642
(2014/09/30)
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- A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides
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The dienamine products formed by the reaction between polysubstituted succinimides and the Petasis reagent were subjected to isomerization under mild acidic conditions to give polysubstituted pyrroles in excellent yields (85-95%). The scope and limitations of this methodology are explored.
- Kobeissi, Marwan,Yazbeck, Ogaritte,Chreim, Yamama
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p. 2523 - 2526
(2014/05/06)
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- Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst
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Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.
- Ali, Md. Ayub,Siddiki, S. M. A. Hakim,Kon, Kenichi,Hasegawa, Junya,Shimizu, Kenichi
-
supporting information
p. 14256 - 14260
(2015/01/09)
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- Synthesis of cyclic imides from nitriles and diols using hydrogen transfer as a substrate-activating strategy
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An atom-economical and versatile method for the synthesis of cyclic imides from nitriles and diols was developed. The method utilizes a Ru-catalyzed transfer-hydrogenation reaction in which the substrates, diols, and nitriles are simultaneously activated into lactones and amines in a redox-neutral manner to afford the corresponding cyclic imides with evolution of H2 gas as the sole byproduct. This operationally simple and catalytic synthetic method provides a sustainable and easily accessible route to cyclic imides.
- Kim, Jaewoon,Hong, Soon Hyeok
-
supporting information
p. 4404 - 4407
(2015/01/08)
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- Porous material-immobilized iodo-Bodipy as an efficient photocatalyst for photoredox catalytic organic reaction to prepare pyrrolo[2,1-a]isoquinoline
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Iodo-Bodipy immobilized on porous silica was used as an efficient recyclable photocatalyst for photoredox catalytic tandem oxidation-[3+2] cycloaddition reactions of tetrahydroisoquinoline with N-phenylmaleimides to prepare pyrrolo[2,1-a]isoquinoline.
- Guo, Song,Zhang, Hongli,Huang, Ling,Guo, Zhendong,Xiong, Guang,Zhao, Jianzhang
-
supporting information
p. 8689 - 8691
(2013/09/23)
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- Dehydrogenative amide synthesis: Azide as a nitrogen source
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A new atom-economical strategy to amide linkage from an azide and alcohol liberating hydrogen and nitrogen was developed with an in situ generated ruthenium catalytic system. The reaction has broad substrate generality including diols for the synthesis of cyclic imides.
- Fu, Zhenqian,Lee, Jeongbin,Kang, Byungjoon,Hong, Soon Hyeok
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supporting information
p. 6028 - 6031
(2013/02/22)
-
- Asymmetric bioreduction of activated carbon-carbon double bonds using Shewanella yellow enzyme (SYE-4) as novel enoate reductase
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Shewanella yellow enzyme (SYE-4), a novel recombinant enoate reductase, was screened against a variety of different substrates bearing an activated double bond, such as unsaturated cyclic ketones, diesters, and substituted imides. Dimethyl- and ethyl esters of 2-methylmaleic acid were selectively reduced to (R)-configured succinic acid derivatives and various N-substituted maleimides furnished the desired (R)-products in up to >99% enantiomeric excess. Naturally occurring (+)-carvone was selectively reduced to (-)-cis- dihydrocarvone and (-)-carvone was converted to the diastereomeric product, respectively. Overall SYE-4 proved to be a useful biocatalyst for the selective reduction of activated CC double bonds and complements the pool of synthetic valuable enoate reductases.
- Iqbal, Naseem,Rudroff, Florian,Brigé, Ann,Van Beeumen, Jozef,Mihovilovic, Marko D.
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experimental part
p. 7619 - 7623
(2012/09/07)
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- Aerobic amide bond formation with N-hydroxysuccinimide
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Breathe easy: Molecular oxygen is one of the most abundant, atom-efficient, and economical oxidants. An aerobic oxidative amide formation from aldehydes and amines is reported. The method uses a catalytic amount of Co(OAc) 2 and N-hydroxysuccinimide as reaction promoters. It is applicable to chiral substrates without loss of their optical purity. Copyright
- Yao, Haoyi,Yamamoto, Kana
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scheme or table
p. 1542 - 1545
(2012/09/08)
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- PROCESS OF FORMING A CYCLIC IMIDE
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A process is provided for the synthesis of a cyclic imide. A primary amine and a diol compound are contacted in the presence of a Ruthenium (II) complex. The Ruthenium (II) catalyst includes at least one of an alicyclic ligand, an aromatic ligand, an arylalicyclic ligand, an arylaliphatic ligand and a phosphine ligand.
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Page/Page column 5; 25; 28-29
(2012/01/15)
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- Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
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The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.
- Sortino,Garibotto,Cechinel Filho,Gupta,Enriz,Zacchino
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p. 2823 - 2834
(2011/06/21)
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- Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2- ones from available reagents
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The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.
- Sadovoy,Kovrov,Golubeva,Sviridova
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p. 1215 - 1223
(2011/10/09)
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- A mild and facile synthesis of cyclic imides using pyridinium chlorochromate
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A mild and facile synthetic method of cyclic imides is presented. These compounds are widely used in the synthesis of novel medical, polymeric, photonic and electronic materials. Compared with traditional syntheses, the method reported has several advantages including mild conditions, simplified work-up and low cost.
- Yang, Yanyan,Wang, Ge,Cao, Xiaohui,Yan, Xilong,Chen, Ligong
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p. 657 - 658,2
(2020/07/30)
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- Microbial decyanation of 1-benzylpyrrolidine-2,5-dicarbonitrile. Mechanistic investigations
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Various bacterial and fungal strains were screened for their ability to catalyse the regioselective hydrolysis of 1-benzylpyrrolidine-2,5-dicarbonitrile (1). Among the examined strains, Rhodococcus opacus sp-lma whole cells transformed both isomers of 1 into 1-benzyl-5-cyano-2-pyrrolidinone (2) and N-benzylacetamide (3). These reactions are difficult to achieve chemically and the synthesis of compound 2 did not compete with microbiological catalysis in terms of efficiency and respect for the guidelines of green chemistry. To distinguish between an oxidative or hydrolytic based-mechanism, the origin of the oxygen atom in 2 was investigated by using 18O2 and 18OH2 coupled with GC-MS analysis. These experiments confirmed that the oxygen atom in 2 came from water and not from molecular oxygen. The reaction is probably initiated by the dehydrogenation of 1 to generate the iminium ion, which could be trapped by a water molecule to form the cyanohydrin. The cyanohydrin intermediate would spontaneously break down to the γ-lactam product 2. Conversion of 1 to 2 by induced rat liver microsomes suggests the involvement of a Cyt P-450-type enzyme. A mechanism that accounts for the formation of 3 is also proposed.
- Pinheiro, Lucimar,Buisson, Didier,Cortial, Sylvie,Delaforge, Marcel,Ouazzani, Jamal
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scheme or table
p. 211 - 215
(2011/09/19)
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- Comparison of microwave-assisted and conventional preparations of cyclic imides
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Microwave-assisted preparation of several cyclic imides was performed with four different cyclic anhydrides. All the reactions are significantly faster and the isolated yields are significantly higher compared to conventionally heated reactions. Furthermore, many of these reactions can be performed with a minimal amount of solvent, thereby enabling the synthetic chemist to obtain high quantities of pure cyclic imides in a matter of hours.
- Upadhyay, Sunil K.,Pingali, Subramanya R.K.,Jursic, Branko S.
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experimental part
p. 2215 - 2217
(2010/05/18)
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- CHEMICAL COMPOUNDS
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The invention is directed to 6-(4-pyι?midinyl)-1 H-indazole derivatives. Specifically, the invention is directed to compounds according to Formula (I) wherein R1 - R4 are defined herein. The compounds of the invention are inhibitors of PDK1 and can be useful in the treatment of immune and metabolic diseases and disorders characterized by constitutively activated ACG kinases such as cancer and more specifically cancers of the breast, colon, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PDK1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
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Page/Page column 139
(2010/07/10)
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- CHEMICAL COMPOUNDS
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The invention is directed to to substituted indazole derivatives. Specifically, the invention is directed to compounds according to Formula I: wherein R1 - R6 and X are defined herein. The compounds of the invention are inhibitors of PDK1 and can be useful in the treatment of disorders characterized by constitutively activated ACG kinases such as cancer and more specifically leukemia and cancers of the breast, colon, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PDK1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
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Page/Page column 56-57
(2010/11/04)
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- Synthesis of cyclic imides from simple diols
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There's something imide so strong: Cyclic imides were synthesized from simple diols with primary amines in a single step using an in-situ-generated ruthenium catalytic system. The atom-economical and operatively simple syntheses of succinimides, phthalimides, and glutarimides, which are important building blocks in natural products and drugs, was also demonstrated. Copyright
- Zhang, Jian,Senthilkumar, Muthaiah,Ghosh, Subhash Chandra,Hong, Soon Hyeok
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supporting information; experimental part
p. 6391 - 6395
(2010/11/05)
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- Polyethylene glycol as a nonionic liquid solvent for the synthesis of N-alkyl and N-arylimides
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Polyethylene glycol (PEG) an inexpensive, nontoxic, environmentally friendly reaction medium for the synthesis of N-alkyl and N-arylphthalimides to afford the corresponding adducts in excellent yields under mild reaction conditions. The use of PEG avoids the use of acidic or basic catalysts, and moreover PEG could be recovered and reused.
- Liang, Jun,Lv, Jing,Fan, Ji-Cai,Shang, Zhi-Cai
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experimental part
p. 2822 - 2828
(2009/12/03)
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