- Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides
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Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heteroc
- George, Michael W.,Hanson-Heine, Magnus W. D.,Harrowven, David C.,Kayal, Surajit,Light, Mark E.,Raimbach, William A. T.,Sun, Wei,Sun, Xue-Zhong
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p. 1546 - 1549
(2022/02/14)
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- Preparation method of N-alkyl phthalimide
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The invention discloses a preparation method of N-alkyl phthalimide. The method comprises the steps: taking phthalic anhydride as a raw material, taking an aqueous solution of alkylamine as an imidization reagent ( no other reagents do not need to be added), and directly synthesizing the N-alkyl phthalimide, wherein the yield is high (96% or above), and the purity is high (99% or above). The preparation method is loose in reaction condition, simple in step and easy to implement; no organic solvent is needed, no other substances are discharged except water, and the method is green, free of pollution and suitable for industrial production.
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Paragraph 0021-0022; 0027-0030
(2021/03/13)
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- Method for constructing N-isopropylphthalimide in one step by using imine as starting material
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The invention discloses a method for constructing N-isopropylphthalimide in one step by using imine as a starting material. According to the method, (E)-N-isopropyl-1-phenylmethylenimine is used as areaction raw material and subjected to a carbonylation reaction to construct N-isopropylphthalimide in one step. The method has the characteristics of mild reaction conditions, simple operation procedures and excellent yield.
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Paragraph 0022; 0023; 0024; 0035; 0036; 0037; 0038; 0041
(2019/01/24)
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- PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
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A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
- Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
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p. 1180 - 1185
(2019/01/26)
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- Method for synthesizing N-isopropylphthalimide
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The invention discloses a method for synthesizing N-isopropylphthalimide. Phthalimide and propylene used as main reaction substrates undergo a nucleophilic addition reaction under the catalysis of a catalyst at a reaction temperature of 50-200 DEG C for 1-30 h to obtain the N-isopropylphthalimide, wherein a molar ratio of phthalimide to propylene in the reaction system is 1:1 to 1:10. The phthalimide and propylene used in the method are all cheap and easily-available raw materials, and the method also has the advantages of mild reaction conditions, no byproducts in the process, high conversionrate and low production cost. The content of normal bodies can reach 98% or more.
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Paragraph 0024; 0046-0051
(2018/09/28)
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- Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
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Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
- Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
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p. 104 - 112
(2018/02/19)
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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supporting information
p. 6404 - 6407
(2017/12/08)
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- N-Heterocyclic carbene-mediated redox condensation of alcohols
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N-Heterocyclic carbenes (NHCs) with a variety of oxidants promote the Mitsunobu-type coupling reactions of alcohols with phenols, carboxylic acids, and phthalimide. Experiments using a chiral alcohol indicate that these reactions proceed via SN1 or SN2 pathways depending on the polarity of the used solvents. The NHCs are consumed as reducing reagents to form their oxides as readily separable byproducts.
- Kato, Terumasa,Matsuoka, Shin-Ichi,Suzuki, Masato
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supporting information
p. 8569 - 8572
(2016/07/13)
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- Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides
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A novel method for the preparation of amides and phthalimides has been developed. The process involves a palladium catalyzed aminocarbonylation of an aryl halide, using a carbodiimide and formic acid as the carbonyl source. Experimental data suggest that the mechanistic pathway for this process involves in-situ generation of carbon monoxide from the reaction of formic acid with a carbodiimide in the presence of a palladium catalyst. The method can be used to produce a variety of amides and N-substituted phthalimides efficiently.
- Seo, Yong-Sik,Kim, Dong-Su,Jun, Chul-Ho
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supporting information
p. 3508 - 3512
(2016/12/26)
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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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- 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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- Practical synthesis of phthalimides and benzamides by a multicomponent reaction involving arynes, isocyanides, and CO2/H2O
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Transition-metal-free multicomponent reactions involving arynes and isocyanides with either CO2 or H2O have been reported. With CO2 as the third component, the reactions resulted in the formation of N-substituted phthalimides. The utility of water as the third component furnished benzamide derivatives in moderate to good yields. These reactions took place under mild conditions with broad scope.
- Kaicharla, Trinadh,Thangaraj, Manikandan,Biju, Akkattu T.
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supporting information
p. 1728 - 1731
(2014/04/17)
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- Efficient synthesis of 2-substituted phthalimides from phthalic acids in one step
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Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications. Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The developed methods are fast, general, high-yielding, do not use additives, and are based on 1:1 molar ratios.
- Chorell, Erik,Chorell, Elin
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supporting information
p. 7512 - 7516
(2013/12/04)
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- Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones
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Figure Persented: Herein we describe a general three-step synthesis of 4-substituted chlorophthalazines in good overall yields. In the key step, N,N-dimethylaminophthalimide (8a) directs the selective monoaddition of alkyl, aryl, and heteroaryl organometallic reagents to afford 3-substituted 3-hydroxyisoindolinones 9b, 9i-9am. Many of these hydroxyisoindolinones are converted to chlorophthalazines 1b-1v via reaction with hydrazine, followed by chlorination with POCl3. We have also discovered two novel transformations of 3-vinyl- and 3-alkynyl-3-hydroxyisoindolinones. Addition of vinyl organometallic reagents to N,N-dimethylaminophthalimide (8a) provided dihydrobenzoazepinediones 15a-15c via the proposed ring expansion of 3-vinyl-3-hydroxyisoindolinone intermediates. 3-Alkynyl-3-hydroxyisoindolinones react with hydrazine and substituted hydrazines to afford 2-pyrazolyl benzoic acids 16a-16d and 2-pyrazolyl benzohydrazides 17a-17g rather than the expected alkynyl phthalazinones.
- Nguyen, Hanh Nho,Cee, Victor J.,Deak, Holly L.,Du, Bingfan,Faber, Kathleen Panter,Gunaydin, Hakan,Hodous, Brian L.,Hollis, Steven L.,Krolikowski, Paul H.,Olivieri, Philip R.,Patel, Vinod F.,Romero, Karina,Schenkel, Laurie B.,Geuns-Meyer, Stephanie D.
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experimental part
p. 3887 - 3906
(2012/06/30)
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- Rhodium(iii)-catalyzed oxidative carbonylation of benzamides with carbon monoxide
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An efficient strategy for the oxidative carbonylation of aromatic amides via C-H/N-H activation to form phthalimides using an Rh(iii) catalyst has been developed. The reaction shows a preference for C-H bonds of electron-rich aromatic amides and tolerates a variety of functional groups. The Royal Society of Chemistry 2011.
- Du, Ya,Hyster, Todd K.,Rovis, Tomislav
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p. 12074 - 12076
(2011/12/14)
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- 2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
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An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.
- Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
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supporting information; experimental part
p. 1380 - 1382
(2010/09/05)
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- Efficient synthesis of aryl hydroxylactams by reducing imides with activated zinc dust
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A series of aryl hydroxylactams (2a, 2b, 2d-2g, 2i-2k, 2m, and 2n) was synthesized by partially reducing aryl cyclic imides in moderate to excellent yields with activated zinc dust alone in acetic acid. This method was regiospecific and can be employed as an alternative for reported methods to partially reduce aryl cyclic imides. Copyright Taylor & Francis Group, LLC.
- Yuan, Xiu-Hua,Zhang, Min-Jie,Kang, Chuan-Qing,Guo, Hai-Quan,Qiu, Xue-Peng,Gao, Lian-Xun
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p. 435 - 444
(2007/10/03)
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- Organic Reactions in Ionic liquids: N-Alkylation of Phthalimide and Several Nitrogen Heterocycles
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N-Alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in ionic liquids ([bmim]BF4= 1-butyl-3-methylimidazolium te trafluoroborate, [bmim]PF6 = 1-butyl-3-methylimidazolium hexafluorophosphate, [buPy]BF4 = butylpyridiniurri tetrafluoroborate) in the presence of potassium hydroxide as a base. In this manner, phthalimide, indole, benzimidazole, succinimide can be successfully alkylated. The procedure is convenient, efficient, and generally affords the N-alkylated product exclusively.
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 208 - 212
(2007/10/03)
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- Organic reactions in ionic liquids: N-alkylation of cyclic imides with alkyl halides promoted by potassium fluoride
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An ionic liquid based on 1-butyl-3-methylimidazolium hexafluorophosphate is used as an efficient reusable reaction medium in the N-alkylation of cyclic imides with alkyl halides promoted by fluoride ion.
- Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
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p. 276 - 278
(2007/10/03)
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- Fluorous Mitsunobu reagents and reactions
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A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse.
- Dandapani, Sivaraman,Curran, Dennis P.
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p. 3855 - 3864
(2007/10/03)
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- N-Alkylation of anilines, carboxamides and several nitrogen heterocycles using CsF-Celite/alkyl halides/CH3CN combination
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It has been found that the N-alkylation of aniline, carboxamides and heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen can be accomplished with alkyl halides in acetonitrile and cesium fluoride-celite employed as a solid base. In this manner, pyrrole, indole, pyrazole, imidazole, benzimidazole, carbazole, phthalimide, indazole, indoline, 2-pyrrolidinone, piperidine and 1,2,4-triazole can be successfully alkylated. The procedure is convenient, efficient and generally gives rise to the N-alkylated product exclusively.
- Hayat, Safdar,Atta-Ur-Rahman,Iqbal Choudhary,Khan, Khalid Mohammed,Schumann, Wilhelm,Bayer, Ernst
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p. 9951 - 9957
(2007/10/03)
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- Mitsunobu reaction modifications allowing product isolation without chromatography: Application to a small parallel library
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Readily available reagents, triphenylphosphine resin and di-t- butylazodicarboxylate, were used in Mitsunobu reactions and the byproducts were removed without chromatography. The new modification was utilized to prepare a small, parallel, solution phase library. (C) 2000 Elsevier Science Ltd.
- Pelletier, Jeffrey C.,Kincaid, Scott
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p. 797 - 800
(2007/10/03)
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- 3-Chloro-3-(dimethoxyphosphoryl)isobenzofuran-l(3h)-one - a new reagent for the rapid, convenient phthaloylation of amines and amino acids in high yields
-
3-Chloro-3-(dimethoxyphosphoryl)isobenzofuran-l(3fl)one (1) reacts rapidly with aliphatic amines and with amino acids at room temperature to give phthalimides in high yields.
- Kehler, Jan,Breuer, Eli
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p. 1419 - 1420
(2007/10/03)
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- Novel heterocyclic ring-expansion and/or dehydration-hydration reactions of propargylic and allenylic hydroxy γ-lactams in the presence of strong base or Lewis acid
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Dehydration-hydration products were obtained in good yields by the treatment of propargylich hydroxy γ-lactams with some Lewis acids. Several propargylic and allenylic hydroxy γ-lactams were successfully converted to the corresponding ring-expanded benzazepines in various yields via a tandem decyclization-cyclization process in the presence of (TMS)2NLi, (TMS)2NNa, or n-BuLi under reflux conditions in THF.
- Jeong, Ill-Yun,Lee, Woo Song,Goto, Satoru,Sano, Shigeki,Shiro, Motoo,Nagao, Yoshimitsu
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p. 14437 - 14454
(2007/10/03)
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- Nucleophilic reactions of N-hydroxy-,methoxy-,2,3-epoxypropoxy-phthalimides
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Reaction of N-hydroxyphthalimide (4) with equivalent amounts of aliphatic and aromatic primary amines gives the N-substituted phthalimides (7), while with excess of these amines if gives the diamides (8) of phthalic acid.The reaction of 4 with t-butyl amine gives only the butyl monoamide (9a) of phthaloylhydroxamic acid.N-Methoxyphthalimide (5) reacts in the same manner.Compound 4 does not condense with epichlorohydrin, but condense with epibromohydrin to give N-(2,3-epoxypropoxy)phthalimide (6) which on reaction with equivalent amounts of aliphatic primary amines gives the N-substituted phthalimides (7) and with excess of the amines it gives the diamides (8) of phthalic acid.The reaction of 6 with aromatic primary amines gives only the N-arylphthalimides.Secondary amines do not react with 6.
- Ranadive, V. B.,Khadilkar, B. M.,Samant, S. D.
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p. 1175 - 1177
(2007/10/02)
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- On the Reaction of α-Chlorobenzylic Cations with Isocyanates
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Isocyanates react as N-nucleophiles with α-chlorobenzylic cations (2) to give 1-oxoisoindolium salts (5).From the reaction of benzotrichlorides with SbCl5 and isocyanates the extremely reactive hexachloroantimonates 5 with R2=Cl are isolated.Hydrolysis of these cyclic N-acyl iminium salts affords phthalimides 6.Reaction of 5k with dimethylcyanamide gives the 2-azoniaallene salt 13. p-Tolyl isocyanate is Friedel-Crafts alkylated by p-chlorobenzotrichloride (1i) in the presence of SbCl5 to furnish the 1,3-oxadiazonium salt 7, which is hydrolyzed to give the benzophenone 9.With ethanol the acetals 10 and 11 are formed from 7.
- Ismail, A. El-Hamid,Hamed, A.,Abdel-Aal, M. Taha,Zeid, I.,Al-Talib, M.,et al.
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p. 661 - 668
(2007/10/02)
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- EFFETS DE CRYPTANDS ET ACTIVATION DE BASES-Va ACTION DES HYDRURES ALCALINS SUR LES ACIDES FAIBLES-II. ALKYLATION DES ANIONS OBTENUS
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Phenoxides, alkoxides and potassium amidates generated by KH in THF or benzene at room temperature are easily alkylated in the presence of catalytic quantities of crytand, without affecting addition-elimination ratios.Thus, Williamson and Gabriel syntheses, as well as the alkylation of secondary amines, occur readily in mild conditions.
- Pasquini, M. A.,Goaller, R. Le,Pierre, J.L.
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p. 1223 - 1226
(2007/10/02)
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