A one-pot, three-component and solvent-free synthesis of 2,3-disubstituted isoindolin-1-ones

被引：19
作者：
Adib, Mehdi [1 ]
Peytam, Fariba [1 ]
Zainali, Mohsen [1 ]
Zhu, Long-Guan [2 ]
Wu, Jing [2 ]
机构：
[1] Univ Tehran, Sch Chem, Coll Sci, Tehran, Iran
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 33期
基金：
美国国家科学基金会;
关键词：
Multi-component reactions; 2,3-Disubstituted isoindolin-1-ones; 2-Formylbenzoic acid; Cyclic six-membered beta-dicarbonyl compounds; Benzylamines; Solvent-free synthesis; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTIONS; FUNCTIONALIZED ISOINDOLINONES; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; DERIVATIVES; ACID; CYCLIZATION; DESIGN;
D O I：
10.1016/j.tetlet.2015.06.020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot and three-component reaction is described for the preparation of 2,3-disubstituted isoindolin-1-ones. Heating a mixture of 2-formylbenzoic acid, a cyclic six-membered beta-dicarbonyl compound, and a benzylamine under solvent-free conditions afforded the title compounds in good to excellent yields. The generality of the reaction was shown by the use of various beta-dicarbonyl compounds including 1,3-cyclohexadione, dimedone, Meldrum's acid, N,N-dimethylbarbituric acid, and some benzylamine derivatives. (C) 2015 Published by Elsevier Ltd.
引用
收藏
页码：4729 / 4732
页数：4
相关论文
共 56 条
[1]   A highly diastereoselective five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Haghshenas, Pouyan ;
Rajai-Daryasarei, Saideh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON LETTERS, 2014, 55 (36) :4983-4986
[2]   Solvent-free and three-component synthesis of 1H,6H-6λ5-[1,2]benzoxaphospholo[2,3-b][1,2]benzoxaphosphol-1-ones [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Bagheri, Mehdi ;
Bijanzadeh, Hamid Reza ;
Amanlou, Masoud .
TETRAHEDRON, 2012, 68 (15) :3237-3242
[3]   One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Rezaei, Narjes .
TETRAHEDRON LETTERS, 2011, 52 (25) :3191-3194
[4]   Solvent-Free Reaction between Anthranilic Acids and Isocyanides: A Novel Approach for the Synthesis of 2-Unsubstituted 4(3H)-Quinazolinones [J].
Adib, Mehdi ;
Karimzadeh, Morteza ;
Mahdavi, Mohammad ;
Sheikhi, Ehsan ;
Mirzaei, Peiman .
SYNLETT, 2011, (06) :834-836
[5]   Reaction between N-Isocyaniminotriphenylphosphorane, Aldimines, Meldrum's Acid and Water: Diastereoselective Synthesis of 3,4-Disubstituted N-Aminopyrrolidine-2,5-diones [J].
Adib, Mehdi ;
Ansari, Samira ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2011, (05) :619-622
[6]   A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives [J].
Allin, SM ;
Northfield, CJ ;
Page, MI ;
Slawin, AMZ .
TETRAHEDRON LETTERS, 1999, 40 (01) :143-146
[7]   Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid [J].
Angel Reyes-Gonzalez, Miguel ;
Zamudio-Medina, Angel ;
Ordonez, Mario .
TETRAHEDRON LETTERS, 2012, 53 (43) :5756-5758
[8]   Electrochemically Initiated Tandem and Sequential Conjugate Addition Processes: One-Pot Synthesis of Diverse Functionalized Isoindolinones [J].
Antico, Pasqualmorica ;
Capaccio, Vito ;
Di Mola, Antonia ;
Massa, Antonio ;
Palombi, Laura .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) :1717-1724
[9]   Molecular basis of peripheral vs central benzodiazepine receptor selectivity in a new class of peripheral benzodiazepine receptor ligands related to alpidem [J].
Anzini, M ;
Cappelli, A ;
Vomero, S ;
Giorgi, G ;
Langer, T ;
Bruni, G ;
Romeo, MR ;
Basile, AS .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) :4275-4284
[10]  
Bergman J., 2008, COMPREHENSIVE HETERO, V3, P269
123456