Graphene Oxide Catalyzed C-N/C-S/[3+2] Cyclization Cascade for Green Synthesis of Thiazolidinone in Water

被引:3
作者
Mahata, Suhasini [1 ]
Sahu, Anjumala [1 ]
Shukla, Prashant [2 ]
Rai, Ankita [2 ]
Singh, Manorama [1 ]
Rai, Vijai K. [1 ]
机构
[1] Guru Ghasidas Vishwavidyalaya, Dept Chem, Bilaspur 495009, Chhattisgarh, India
[2] Jawaharlal Nehru Univ, Sch Phys Sci, New Delhi 110029, India
关键词
Graphene oxide; imine; mercaptoacetic acid; water; organic; 1,3-thiazolidin-4-one; ONE-POT SYNTHESIS; SELECTIVE-INHIBITION; 4-THIAZOLIDINONES; EFFICIENT; CARBOCATALYST; MICROWAVE; ACID; ACTIVATION; CHEMISTRY; ANALOGS;
D O I
10.2174/1570178614666171002145250
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, first graphene oxide catalyzed one-pot three-component green synthesis of 1,3-thiazolidin-4-one using amine, aldehyde and mercapto acetic acid in water has been reported. The reaction is affected via sequential C-N and C-S bond formation and ring transformation reactions leading to thiazolidin-4-ones formation. The use of water as solvent at room temperature, good to excellent yields of pure products (75-92%) and operational simplicity are the salient features of the envisaged protocol. The graphene oxide catalyst is very mild, effective and most of its activity is preserved after being reused for five times.
引用
收藏
页码:665 / 672
页数:8
相关论文
共 67 条
[41]   [2+2] Annulation of Aldimines with Sulfonic Acids: A Novel One-Pot cis-Selective Route to β-Sultams [J].
Rai, Ankita ;
Rai, Vijai K. ;
Singh, Atul K. ;
Yadav, Lal Dhar S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (23) :4302-4306
[42]   First iodine/IL-catalyzed carbohydrate activation as aldehyde equivalent for [C+2C+N] construction of β-lactam ring [J].
Rai, Vijai K. ;
Sharma, Bhaskar ;
Sharoff, Vidya R. ;
Rai, Ankita .
TETRAHEDRON LETTERS, 2016, 57 (30) :3260-3263
[43]   The first NHC-induced regioselective introduction of C- and N-nucleophiles in to Baylis-Hillman enals [J].
Rai, Vijai K. ;
Sahu, Ganeshwar P. ;
Rai, Ankita .
TETRAHEDRON LETTERS, 2015, 56 (21) :2664-2668
[44]   Predicting anti-HIV activity of 1,3,4-thiazolidinone derivatives: 3D-QSAR approach [J].
Ravichandran, V. ;
Kumar, B. R. Prashantha ;
Sankar, S. ;
Agrawal, R. K. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) :1180-1187
[45]   Design and synthesis of 2-(2,6-dibromophenyl)-3-heteroaryl-1, 3-thiazolidin-4-ones as anti-HIV agents [J].
Rawal, Ravindra K. ;
Tripathi, Rajkamal ;
Katti, S. B. ;
Pannecouque, Christophe ;
De Clercq, Erik .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (12) :2800-2806
[46]  
Rawal RK, 2004, J CHEM RES, P368
[47]   Graphene oxide (GO)-catalyzed chemoselective thioacetalization of aldehydes under solvent-free conditions [J].
Roy, Babli ;
Sengupta, Debasish ;
Basu, Basudeb .
TETRAHEDRON LETTERS, 2014, 55 (48) :6596-6600
[48]   Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones [J].
Saiz, Cecilia ;
Pizzo, Chiara ;
Manta, Eduardo ;
Wipf, Peter ;
Mahler, S. Graciela .
TETRAHEDRON LETTERS, 2009, 50 (08) :901-904
[49]  
Shah T.J., 2007, ARCH ORG CHEM, VXIV, P218
[50]   A study of anti-inflammatory activity of some novel α-amino naphthalene and β-amino naphthalene derivatives [J].
Sharma, S ;
Singh, T ;
Mittal, R ;
Saxena, KK ;
Srivastava, VK ;
Kumar, A .
ARCHIV DER PHARMAZIE, 2006, 339 (03) :145-152