- Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights
-
A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.
- Wu, Qiuyue,Dong, Ziyang,Xu, Jiaxi,Yang, Zhanhui
-
supporting information
p. 3173 - 3180
(2021/04/21)
-
- Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β’-Keto-β-Amino Esters via Dynamic Kinetic Resolution
-
An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti β’-hydroxy-β-amino esters were obtained in moderate to good yields (60–95%) with 72–99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading (TON up to 9100). (Figure presented.).
- He, Jiayin,Huang, An,Ling, Fei,Wang, Shiliang,Wang, Yifan,Wang, Ze,Zhao, Xianghua,Zhong, Weihui
-
supporting information
p. 4714 - 4719
(2021/09/02)
-
- Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis
-
Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.
- Liu, Hao-Nan,Cao, Hao-Qiang,Cheung, Chi Wai,Ma, Jun-An
-
supporting information
p. 1396 - 1401
(2020/02/22)
-
- Design, Synthesis, and Biochemical Characterization of Non-Native Antagonists of the Pseudomonas aeruginosa Quorum Sensing Receptor LasR with Nanomolar IC50 Values
-
Quorum sensing (QS), a bacterial cell-to-cell communication system mediated by small molecules and peptides, has received significant interest as a potential target to block infection. The common pathogen Pseudomonas aeruginosa uses QS to regulate many of its virulence phenotypes at high cell densities, and the LasR QS receptor plays a critical role in this process. Small molecule tools that inhibit LasR activity would serve to illuminate its role in P. aeruginosa virulence, but we currently lack highly potent and selective LasR antagonists, despite considerable research in this area. V-06-018, an abiotic small molecule discovered in a high-throughput screen, represents one of the most potent known LasR antagonists but has seen little study since its initial report. Herein, we report a systematic study of the structure-activity relationships (SARs) that govern LasR antagonism by V-06-018. We synthesized a focused library of V-06-018 derivatives and evaluated the library for bioactivity using a variety of cell-based LasR reporter systems. The SAR trends revealed by these experiments allowed us to design probes with 10-fold greater potency than that of V-06-018 and 100-fold greater potency than other commonly used N-acyl-l-homoserine lactone (AHL)-based LasR antagonists, along with high selectivities for LasR. Biochemical experiments to probe the mechanism of antagonism by V-06-018 and its analogues support these compounds interacting with the native ligand-binding site in LasR and, at least in part, stabilizing an inactive form of the protein. The compounds described herein are the most potent and efficacious antagonists of LasR known and represent robust probes both for characterizing the mechanisms of LuxR-type QS and for chemical biology research in general in the growing QS field.
- Blackwell, Helen E.,Manson, Daniel E.,Nyffeler, Kayleigh E.,O'Reilly, Matthew C.
-
-
- Two Competitive but Switchable Organocatalytic Cascade Reaction Pathways: The Diversified Synthesis of Chiral Acetal-Containing Bridged Cyclic Compounds
-
The organocatalytic enantioselective synthesis of methanobenzodioxepine derivatives bearing a 6,6,5-bridged ring system is presented. The m-CPBA-triggered in situ α-oxidation of β-oxoesters to provide the required but unstable α-hydroxy-β-dicarbonyl substrates is the key to this three-step sequence, providing the desired cyclic acetals with excellent stereoselectivities containing two bridgehead and one fully substituted stereocenters. It is noteworthy that the absence of m-CPBA furnished the acetal products bearing a 6,6,6-bridged ring system with similar good results from the same starting materials.
- Lv, Xue-Jiao,Chen, Ying-Han,Liu, Yan-Kai
-
supporting information
p. 190 - 195
(2019/01/11)
-
- Inhibitors of Quorum Sensing Receptor LasR
-
Modulation of quorum sensing in Gram-negative bacteria, particularly strains of Pseudomonas which form biofilms, by compounds including those of formula I and formula II: where: AR is optionally substituted phenyl, cycloalkyl or cycloalkenyl or heterocyclic, and R1 is optionally substituted alkyl, alkenyl, alkoxyalkyl, or alkylthioalkyl or alkyl substituted at the omega position with optionally substituted phenyl, cyclohexyl or cyclohexenyl. In particular compounds inhibit quorum sensing and biofilm formation. Pharmaceutical compositions for treatment of bacterial infections and methods of treatment of such infections are provided
- -
-
Paragraph 0198; 0199
(2019/05/07)
-
- Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs
-
The invention discloses a 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound, a tautomer thereof, a pharmaceutical composition thereof and application thereof to drugs. The 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound has double effects of resisting platelet aggregation and protecting nerve cells, and comprises a compound as shown in the formula (I), a tautomer (Ia) thereof, or a stereoisomer, a geometrical isomer, a hydrate or a solvate thereof, or a pharmaceutically acceptable salt or prodrug as shown in the description. The 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound and the pharmaceutical composition thereof provided by the invention can be used for preparing drugs for prevention and/or treatment and/or auxiliary treatment of cerebral apoplexy, cardiovascular and cerebrovascular diseases, senile dementia and complications thereof caused by thrombosis and excessive free radicals.
- -
-
Paragraph 0128; 0143
(2018/10/19)
-
- Substituted phenyl pyrazolone derivatives and preparation and application (by machine translation)
-
The present invention provides a substituted phenyl pyrazolone derivatives, in particular to a 2 - phenyl - pyrazoline - 3 - ketone compound and its pharmaceutically acceptable salt, solvate. The substituted acetic acid ethyl ester with sodium hydroxide in aqueous solution in the [...] reflux reaction, then in the palladium-carbon and hydrogen under the action of the hydrogenolysis benzyl, phenyl [...] obtained, with the bromochlorodifluoromethane alkane reaction to obtain the chloro, finally with the secondary amine on the condensation to obtain the target compound. The invention substituted phenyl pyrazoline compounds in vitro exhibits excellent capability of eliminating the free radicals, and have more strongly inhibit H3 receptor activity, exhibits excellent penetration of the blood brain barrier capacity, has a unique dual active, therefore, its for cerebral apoplexy, Alzheimer's disease, Parkinson's disease, progressive neurodegenerative diseases such as frozen sickness treatment has a unique clinical effect. The compound of the invention for treating central system system related disease and inflammatory disease application of the medicament. The formula structure is as follows: (by machine translation)
- -
-
Paragraph 0034; 0039; 0040
(2019/01/08)
-
- Bromide-Mediated C-H Bond Functionalization: Intermolecular Annulation of Phenylethanone Derivatives with Alkynes for the Synthesis of 1-Naphthols
-
Bromide-mediated intermolecular annulation of phenylethanone derivatives with alkynes has been developed, which allows for the regioselective formation of polysubstituted 1-naphthols. The usage of readily available bromine catalyst, broad substrate scope, and mild conditions make this protocol very practical. Mechanistic investigations reveal that the bromination of phenylethanone derivatives occurs to yield bromo-substituted intermediates, which react in situ with alkynes to furnish the desired 1-naphthols.
- Lu, Tao,Jiang, Ya-Ting,Ma, Feng-Ping,Tang, Zi-Jing,Kuang, Liu,Wang, Yu-Xuan,Wang, Bin
-
supporting information
p. 6344 - 6347
(2017/12/08)
-
- Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC–AuICatalyst
-
Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuIcatalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.
- Tarigopula, Chandrahas,Thota, Ganesh Kumar,Balamurugan, Rengarajan
-
p. 5855 - 5861
(2016/12/18)
-
- Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis
-
The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalyzed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonization/lactamization cascade reaction. Notably, to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90 % ee). The derivatization of the heterocyclic core of a 3,5,6-substituted dihydropyranone through hydrogenation is also reported.
- Stark, Daniel G.,Morrill, Louis C.,Cordes, David B.,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Smith, Andrew D.
-
supporting information
p. 395 - 400
(2016/05/19)
-
- 2 - (3-cyano-4-alkoxy) phenyl-4-substituted thiazole-5- formic acid class compound, composition and its preparation and use
-
The invention relates to a 2-(3-cyano-4-alkoxy) phenyl-4-substituted thiazole-5-formic acid compound which has xanthine oxidase inhibitory activity and is shown in a general formula I, a composition and preparation methods thereof. The invention also relates to applications of the compound and the composition thereof to preparation of medicaments for treating and/or preventing hyperuricemia and gout diseases. In the formula I, R2 is substituted or unsubstituted phenyl or a substituted or unsubstituted heteroaromatic radical, R1 is a substitutive aliphatic group of a straight chain or a branched chain, substituted or unsubstituted alicyclic hydrocarbonyl or substituted or unsubstituted aryl alkyl and A is an oxygen atom, a sulfur atom or a nitrogen atom.
- -
-
Paragraph 0165; 0168; 0169
(2016/10/07)
-
- The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes
-
Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
- Loy, Nicole S. Y.,Choi, Subin,Kim, Sunggak,Park, Cheol-Min
-
supporting information
p. 7336 - 7339
(2016/06/14)
-
- Design, synthesis and RON receptor tyrosine kinase inhibitory activity of new head groups analogs of LCRF-0004
-
New heteroarylcarboxamide head groups substituted with two aromatic rings analogs of thieno[3,2-b]pyridine-based kinase inhibitor LCRF-0004 were designed and synthesized. Potent inhibitors of RON tyrosine kinase with various level of selectivity for c-Met RTK were obtained.
- Raeppel, Franck,Raeppel, Stéphane L.,Therrien, Eric
-
p. 3810 - 3815
(2015/08/24)
-
- A one-pot copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones
-
A one-pot copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones from N-aminopyrroles was developed. This tandem reaction involves a Conrad-Limpach-type reaction, including the thermal condensation of N-aminopyrroles with the carbonyl group of β-oxo esters followed by the cyclization of Schiff base intermediates. Compared to the traditional Conrad-Limpach quinoline synthesis, we herein successfully applied copper(II) as a catalyst in this transformation to furnish 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones for the first time. Most of the substrates bearing electron-donating (EDG) and electron-withdrawing (EWG) groups worked well with this procedure. The corresponding products could be converted directly into diverse pyrrolo[1,2-b]pyridazine for drug discovery and materials science. A copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones from N-aminopyrroles was developed, and the corresponding products could be converted directly into diverse pyrrolo[1,2-b]pyridazine for drug discovery and materials science.
- Tan, Cun,Xiang, Haoyue,He, Qian,Yang, Chunhao
-
supporting information
p. 3656 - 3660
(2015/06/16)
-
- 1,5-Diketones Synthesis via Three-Component Cascade Reaction
-
A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.
- Xing, Li-Juan,Lu, Tao,Fu, Wei-Li,Lou, Mei-Mei,Chen, Bo,Wang, Zhi-Shen,Jin, Yang,Li, Dan,Wang, Bin
-
supporting information
p. 3076 - 3080
(2015/11/03)
-
- QUINOLINONE DERIVATIVES FOR USE IN THE TREATMENT OF AN AUTOIMMUNE DISEASE AND/OR AN INFLAMMATORY DISEASE
-
There is provided compounds of formula I, wherein X1 to X4, R1 to R4, Y1, Y2 and L are as defined in the description, and pharmaceutically-acceptable salts thereof, which may be useful in the treatment and/or prophylaxis of autoimmune diseases, inflammatory (e.g. chronic inflammatory) diseases and/or other diseases that may benefit from production of ROS (reactive oxygen species) by a NADPH oxidase complex.
- -
-
Paragraph 0170; 0171
(2014/02/16)
-
- Stereodivergent total synthesis of (+)-aspergillide B and (+)-7-epi-aspergillide A
-
The stereoselective total syntheses of (+)-aspergillide B and (+)-7-epi-aspergillide A were achieved. The key reactions include Noyori's asymmetric transfer hydrogenation, an Achmatowicz rearrangement, a Ferrier-type alkynylation, a hydrosilylation-protodesilylation, a CBS (Corey-Bakshi-Shibata) oxazaborolidine reduction, a Yamaguchi macrolactonization, and a Mitsunobu macrolactonization. The stereoselective total syntheses of (+)-aspergillide B and (+)-7-epi-aspergillide A were achieved. The key reactions include Noyori's asymmetric transfer hydrogenation, an Achmatowicz rearrangement, a Ferrier-type alkynylation, a hydrosilylation-protodesilylation, a CBS (Corey-Bakshi-Shibata) oxazaborolidine reduction, a Yamaguchi macrolactonization, and a Mitsunobu macrolactonization. Copyright
- Sridhar,Srihari
-
p. 578 - 587
(2013/02/26)
-
- Highly diastereoselective and enantioselective synthesis of α-hydroxy β-amino acid derivatives: Lewis base catalyzed hydrosilylation of α-acetoxy β-enamino esters
-
By design: A series of α-acetoxy-β-enamino esters 1 were synthesized and then subjected to catalytic asymmetric hydrosilylation. In the presence of a chiral Lewis base catalyst, the reactions proceeded smoothly to provide a wide range of chiral α-acetoxy β-amino acid derivatives in high yields with good diastereoselectivities and enantioselectivities. Copyright
- Jiang, Yan,Chen, Xing,Zheng, Yongsheng,Xue, Zhouyang,Shu, Chang,Yuan, Weicheng,Zhang, Xiaomei
-
supporting information; experimental part
p. 7304 - 7307
(2011/09/16)
-
- PYRROLE ANTIFUNGAL AGENTS
-
The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
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-
Page/Page column 79-80
(2009/12/05)
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- NITROGEN CONTAINING HETEROAROMATICS AS FACTOR Xa INHIBITORS
-
The present application describes nitrogen containing heteroaromatics and derivatives thereof of formula (I) or pharmaceutically acceptable salt or prodrug forms thereof, wherein J is N or NH and D may be C(=NH)NH2, which are useful as inhibitors of factor Xa.
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-
Page/Page column 106
(2009/10/01)
-
- Molybdenum(VI) dichloride dioxide catalyzed synthesis of β-keto esters by C-H insertion of ethyl diazoacetate into aldehydes
-
Synthesis of β-keto esters by condensing various aldehydes with ethyl diazoacetate is achieved by using molybdenum(VI) dichloride dioxide. Aromatic, aliphatic, and heterocyclic aldehydes are successfully condensed with ethyl diazoacetate to obtain corresponding β-keto esters in high yields at room temperature.
- Jeyakumar, Kandasamy,Chand, Dillip Kumar
-
p. 1685 - 1687
(2008/12/21)
-
- A novel synthetic method for β-keto esters
-
A novel synthetic method for the preparation of β-keto esters has been developed. α-Phenylseleno acetate was treated with LDA to produce a selenium-stabilised carbanion, which reacted with aldehydes, followed by selenoxide syn-elimination, to give β-keto esters.
- Qian, Hao,Ge, Chunrong,Huang, Xian
-
p. 160 - 161
(2008/02/03)
-
- Substitution of acyl for acetyl with N-acylbenzotriazoles catalyzed by samarium triiodide
-
Catalyzed by samarium triiodide (SmI3), substitution of acyl with N-acylbenzotriazoles for acetyl in acetoacetic esters and acetylacetone proceeds smoothly under neutral conditions in open air, affording the corresponding β-keto esters and β-diketones in good yields. Copyright Taylor & Francis Group, LLC.
- Zou, Xuefei,Jia, Xiaofei,Wang, Xiaoxia,Xie, Guanqun
-
p. 1617 - 1625
(2008/02/01)
-
- Preparation of polystyrene-supported α-seleno acetate and application to solid-phase synthesis of β-keto esters
-
A novel polystyrene-supported α-seleno acetate has been developed. This novel resin was treated with LDA to produce a selenium-stabilized carbanion, which reacted with aldehydes, followed by selenoxide syn-elimination to give β-keto esters. Georg Thieme Verlag Stuttgart.
- Qian, Hao,Huang, Xian
-
p. 1547 - 1548
(2007/10/03)
-
- CuSO4-catalyzed diazo decomposition in water: a practical synthesis of β-keto esters
-
CuSO4 was found to be an efficient catalyst for the diazo decomposition of β-hydroxy α-diazoesters in water. 1,2-H shift occurred efficiently to give β-keto esters in high yields. No O-H bond insertion products were identified.
- Liao, Mingyi,Wang, Jianbo
-
p. 8859 - 8861
(2007/10/03)
-
- Niobium(V) chloride-catalyzed C-H insertion reactions of α-diazoesters: Synthesis of β-keto esters
-
Aldehydes react readily with ethyl diazoacetate in the presence of 5 mol% of NbCl5 in dichloromethane to produce the corresponding β-keto esters in good yields with high selectivity. This method is very useful for the preparation of β-keto esters from both electron-rich as well as electron-deficient aromatic aldehydes under mild reaction conditions.
- Yadav,Subba Reddy,Eeshwaraiah,Reddy
-
p. 875 - 878
(2007/10/03)
-
- 2, 6 BISHETEROARYL-4-AMINOPYRIMIDINES AS ADENOSINE RECEPTOR ANTAGONISTS
-
4-Aminopyrimidine derivatives of formula (I) FORMULA heteroaryl groups, including pharmaceutically acceptable salts thereof, wherein R1 and R2 are adenosine A2A receptor antagonists useful in the treatment of movement disorders such as Parkinson's disease.
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-
Page/Page column 94
(2010/02/12)
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- PYRAZOLE COMPOUNDS
-
The invention relates to compounds of formula (I), in addition to their salts and solvates. In said formula, X, R1, R2, R3, R4, R5 and R 6 are defined as cited in claim 1. Said compounds are suitable for use as ligands of 5 HT receptors.
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-
Page/Page column 22
(2010/02/09)
-
- SUBSTITUTED PYRAZOLE COMPOUNDS
-
The invention relates to compounds of formula (I), in addition to their salts and solvates. In said formula, X, R1, R2, R3, R4 and R5 are defined as cited in claim (1). Said compounds are suitable for use as ligands of 5 HT receptors.
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-
Page/Page column 25-26
(2010/02/09)
-
- Preparation of β-keto esters and β-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles
-
Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-1 are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylati
- Katritzky, Alan R.,Wang, Zuoquan,Wang, Mingyi,Wilkerson, Chavon R.,Hall, C. Dennis,Akhmedov, Novruz G.
-
p. 6617 - 6622
(2007/10/03)
-
- Acid-catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: An investigation on the synthesis of 3-hydroxy-2-arylacrylic acid ethyl esters
-
Several commercial Lewis acids, including those of the Bronsted type, specifically HBF4·OEt2, are able to catalyze the reaction between aromatic aldehydes and ethyl diazoacetate to produce 3-hydroxy-2-arylacrylic acid ethyl esters and 3-oxo-3-arylpropanoic acid ethyl esters. Reactions catalyzed by the iron Lewis acid [(η5-C 5H5)Fe+(CO)2(THF)]BF 4- (i.e., 1) have the best yields and greatest ratio of 3-hydroxy-2-arylacrylic acid ethyl ester. The product distribution of 1 is not affected in the presence of Proton Sponge, but is dependent on temperature and the nature of the substrate aldehyde, whereas the activity of HBF 4-OEt2 is affected by the presence of Proton Sponge and is reactive at temperatures as low as -78 °C. Consequently, both 1 and HBF4·OEt2 are valuable catalysts in producing important 3-hydroxy-2-arylacrylic acid ethyl esters as precursors to biologically active compounds.
- Dudley, Matthew E.,Morshed, Monzur,Brennan, Courtney L.,Islam, M. Shahidul,Ahmad, M. Syarhabil,Atuu, Mary-Rose,Branstetter, Bryan,Hossain, M. Mahmun
-
p. 7599 - 7608
(2007/10/03)
-
- Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction
-
New facile experimental procedures for the preparation of 2,3,4,6-tetrasubstituted pyridines in a single synthetic step have been developed. Thus, an enamino ester and alkynone react by Michael addition-cyclodehydration in a heterocyclisation process that is catalysed by acetic acid, Amberlyst 15 ion exchange resin, zinc(II) bromide or ytterbium(III) triflate. The new one-step Bronsted or Lewis acid-catalysed Bohlmann-Rahtz reaction is a simple, direct and highly expedient method for the synthesis of pyridines that proceeds at a lower reaction temperature and avoids the need to isolate reaction intermediates.
- Bagley, Mark C.,Brace, Christian,Dale, James W.,Ohnesorge, Maren,Phillips, Nathan G.,Xiong, Xin,Bower, Justin
-
p. 1663 - 1671
(2007/10/03)
-
- Parallel synthesis of potent, pyrazole-based inhibitors of Helicobacter pylori dihydroorotate dehydrogenase
-
The identification of several potent pyrazole-based inhibitors of bacterial dihydroorotate dehydrogenase (DHODase) via a directed parallel synthetic approach is described below. The initial pyrazole-containing lead compounds were optimized for potency against Helicobacter pylori DHODase. Using three successive focused libraries, inhibitors were rapidly identified with the following characteristics: Ki 10 000-fold selectivity over human DHODase.
- Haque, Tasir S.,Tadesse, Seifu,Marcinkeviciene, Jovita,Rogers, M. John,Sizemore, Christine,Kopcho, Lisa M.,Amsler, Karen,Ecret, Lisa D.,Zhan, Dong Liang,Hobbs, Frank,Slee, Andrew,Trainor, George L.,Stern, Andrew M.,Copeland, Robert A.,Combs, Andrew P.
-
p. 4669 - 4678
(2007/10/03)
-
- Nitrogen containing heteroaromatics as factor Xa inhibitors
-
The present application describes nitrogen containing heteroaromatics and derivatives thereof of formula I: or pharmaceutically acceptable salt or prodrug forms thereof, wherein J is N or NH and D may be C(=NH)NH2, which are useful as inhibitors of factor Xa.
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-
-
- Simple and high yielding syntheses of β-keto esters catalysed by zeolites
-
Simple and high yielding syntheses of several β-keto esters, catalysed by zeolite Hβ are reported. The methods developed include condensation of aldehydes with ethyl diazoacetate and transesterification of β-keto esters with primary, secondary, allylic and benzylic alcohols etc., all catalysed by Hβ. It was further observed that under microwave irradiation the yields of many aromatic β-keto esters were enhanced appreciably.
- Balaji,Chanda, Bhanu M.
-
p. 13237 - 13252
(2007/10/03)
-
- Rapid dehydrosulfenylation of sulfoxides under microwave irradiation
-
Pyrolytic β-elimination of sulfoxides has been promoted by microwave irradiation. The reaction is very fast and yields are almost quantitative.
- Matloubi Moghaddam, Firouz,Ghaffarzadeh, Mohammad
-
p. 1855 - 1858
(2007/10/03)
-
- A process for the synthesis of βketoesters using in-situ generated (trimethylsilyl)malonates
-
(TMS)ethyl malonate can be generated in-situ by treating potassium ethyl malonate with trimethylsilyl chloride and acylated with aliphatic or aromatic acyl imidazoles or chlorides in the presence of DBU to prepare a variety of β-ketoesters. This constitutes a high yield method for preparing β-ketoesters, which also can be extended to the formation of alkylidene malonates.
- Wang, Xui,Monte, William T.,Napier, James J.,Ghannam, Ameen
-
p. 9323 - 9326
(2007/10/02)
-
- Studies on Pyrazines. 17. . An Efficient Synthesis of Pteridine-6-carboxylic Acids
-
2,4-Diaminopteridine-6-carboxylic acid (1) and pterin-6-carboxylic acid (2) were prepared by permanganate oxidation of the corresponding 6-(2-furyl)-substituted pteridines under much milder conditions.Several attempts to cleave the furan ring with other oxidizing agents are also described.
- Sato, Nobuhiro,Saito, Noriko
-
p. 1737 - 1740
(2007/10/02)
-
- 4-quinolone derivatives having anti-inflammatory, anti-allergic, antitussive, expectorant and antithrombotic activity
-
4-Quinolone derivatives of the present invention are useful for their anti-inflammatory, anti-allergenic, antitussive, expectorant and antithrombotic activity. Pharmaceutical compositions containing said compounds and pharmaceutically acceptable salts thereof and methods of treating humans and animals are described herein.
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