The First Solvent-Free, Microwave-Accelerated, Three-Component Synthesis of Thiazolidin-4-ones via One-Pot Tandem Staudinger/aza-Wittig Reaction

被引：7

作者：

Shanmugavelan, Poovan ^{[1
]}

Sathishkumar, Murugan ^{[1
]}

Nagarajan, Sangaraiah ^{[1
]}

Ranganathan, Raja ^{[1
]}

Ponnuswamy, Alagusundaram ^{[1
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2014年 / 51卷 / 04期

关键词：

BIOLOGICAL-ACTIVITY; IONIC LIQUID; 4-THIAZOLIDINONES; CONSTRUCTION; ANTIFUNGAL; LIBRARY; ACID;

D O I：

10.1002/jhet.1705

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and rapid, solvent-free, microwave-accelerated, one-pot, three-component protocol for thiazolidin-4-ones synthesis from organic azides has been reported for the first time via Staudinger/aza-Wittig reaction. The microwave-accelerated, solvent-free approach overcomes the limitations associated with the prevailing solution phase methodologies. In particular, its novelty is that it eradicates the vital limitation, that is, accumulation of water (byproduct) that is known to affect the yield and rate of the reaction. Thus, a library of thiazolidin-4-ones has been synthesized in short time in excellent yields (92-96%).

引用

页码：1004 / 1011

页数：8

共 47 条

[31] A green one-pot three-component synthesis of -aminophosphonates under solvent-free conditions and ultrasonic irradiation using Fe3O4@SiO2-imid-PMAn as magnetic catalyst [J].

Esmaeilpour, Mohsen ;

Zahmatkesh, Saeed ;

Javidi, Jaber ;

Rezaei, Elahe .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (05) :530-537

[32] IONIC LIQUID-CATALYZED ONE-POT SYNTHESIS OF 1H-PYRANO[2,3-d]PYRIMIDIN-2(8aH)-ONE DERIVATIVES VIA THREE-COMPONENT REACTION UNDER SOLVENT-FREE CONDITIONS [J].

Guo, Hong-Yun ;

Li, Xiao-Jun ;

Yu, Yi .

SYNTHETIC COMMUNICATIONS, 2012, 42 (20) :3011-3020

[33] Synthesis of acenaphtho[1′,2′:4,5]pyrrolo[2,3-d]pyrimidine derivatives via one-pot three-component reaction [J].

Amiri, Zeinab ;

Bayat, Mohammad .

MONATSHEFTE FUR CHEMIE, 2021, 152 (10) :1291-1296

[34] Choline hydroxide promoted sustainable one-pot three-component synthesis of 1H-pyrazolo[1,2-a]pyridazine-2-carbonitriles under solvent-free conditions [J].

Vajekar, Shailesh N. ;

Shankarling, Ganapati S. .

SYNTHETIC COMMUNICATIONS, 2020, 50 (08) :1147-1158

[35] Parallel Synthesis of Pyrrolo[3,2-f]quinolines (PQQ Skeleton) Library via a One-Pot Three-Component Reaction under Catalyst-Free Conditions [J].

Ma, Ning ;

Zhang, Mei-Mei ;

Wang, Xiang-Shan .

POLYCYCLIC AROMATIC COMPOUNDS, 2016, 36 (05) :683-696

[36] Efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-e][1,4]thiazepine]dione via three-component reaction [J].

Chen, Hui ;

Shi, Daqing .

TETRAHEDRON, 2011, 67 (31) :5686-5692

[37] Efficient synthesis of some novel pyrimido[4,5-e][1,3]oxazine dione derivatives via one-pot three-component reaction under thermal and thermal microwave-assisted conditions [J].

Asadi, Sara ;

Mehrabi, Hossein .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (03) :497-503

[38] Efficient, Concise, and Chemoselective Synthesis of 1H-Benzo[f]indole-4,9-dione with 4-Hydroxycoumarin Substituent via a One-Pot Three-Component Reaction [J].

Alizadeh, Abdolali ;

Hasanpour, Hamidreza ;

Rezaiyehraad, Reza .

CHEMISTRYSELECT, 2023, 8 (48)

[39] (NH4)2.5H0.5PW12O40-catalyzed rapid and efficient one-pot synthesis of dihydropyridines via the Hantzsch reaction under solvent-free conditions [J].

Ghattali, Seyyed Naeim ;

Saidi, Kazem ;

Khabazzadeh, Hojatollah .

RESEARCH ON CHEMICAL INTERMEDIATES, 2014, 40 (01) :281-291

[40] Durable magnetite-chitosan core-shell nanoparticles as reusable green nanocatalyst for the benign one-pot three-component synthesis of spirooxindoles and spirochromenes at ambient temperature under both solvent-free and ultrasonic conditions in aqueous ethanol solution [J].

Mardaneh, Pegah ;

Sardarian, Ali Reza .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2024, 21 (01) :211-225

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