Efficient synthesis of novel spiro[indole-3,6′-pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives through an organobase-catalyzed, three-component reaction

被引：25

作者：

Esmaeili, Abbas Ali ^{[1
]}

Amini-Ghalandarabad, Saeid ^{[2
]}

Mesbah, Fariba ^{[2
]}

Tasmimi, Masoud ^{[2
]}

Izadyar, Mohammad ^{[1
]}

Fakhari, Ali Reza ^{[3
]}

Salimi, Ali Reza ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Dept Chem, Mashhad, Iran

[2] Univ Birjand, Dept Chem, Birjand, Iran

[3] Shahid Beheshti Univ, Dept Chem, Fac Sci, GC, Tehran, Iran

来源：

TETRAHEDRON | 2015年 / 71卷 / 16期

关键词：

Spirooxindole; Malononitrile; Three-component reactions; Pyranothiazolopyrimidine; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; C-H; CONSTRUCTION; PYRIMIDINE; ISATIN; THIAZOLOPYRIMIDINES; SPIROOXINDOLES; OXINDOLES; ANALOGS;

D O I：

10.1016/j.tet.2015.01.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fast and convenient protocol for the synthesis of novel spirooxindole derivatives in excellent yields was developed by the three-component reactions of malononitrile, isatin, and 2,3-dihydro-5H-[1,3]thiazolo [3,2-a]pyrimidine-5,7(6H)-dione in the presence of diisopropylethylamine. (C) 2015 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2458 / 2462

页数：5

相关论文

共 69 条

[1] Synthesis, Antioxidant, Antituomer Activities of Some New Thiazolopyrimidines, Pyrrolothiazolopyrimidines and Triazolopyrrolothiazolopyrimidines Derivatives [J].

Abu-Hashem, Ameen Ali ;

Youssef, Mohamed M. ;

Hussein, Hoda A. R. .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2011, 58 (01) :41-48

[2] Diblydropyrido[2,3-d]pyrimidines as a new class of antfleishmanial agents [J].

Agarwal, A ;

Ramesh ;

Ashutosh ;

Goyal, N ;

Chauhan, PMS ;

Gupta, S .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (24) :6678-6684

[3] Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions [J].

Albertshofer, Klaus ;

Tan, Bin ;

Barbas, Carlos F., III .

ORGANIC LETTERS, 2012, 14 (07) :1834-1837

[4] Counter-Current Chromatography Separation of Isatin Derivatives using the Sandmeyer Methodology [J].

Almeida, Marcia R. ;

Leitao, Gilda G. ;

Silva, Barbara V. ;

Barbosa, Jussara P. ;

Pinto, Angelo C. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (04) :764-769

[5]

[Anonymous], EUR J EPIDEMIOL

[6] Synthesis of Novel Vicinal Coumarin- and Oxindole-Functionalized Dispiropyrrolidines and Dispiropyrrolizidines via [3+2]-Cycloaddition Reactions [J].

Bakthadoss, Manickam ;

Kannan, Damodharan ;

Sivakumar, Govindan .

SYNTHESIS-STUTTGART, 2012, 44 (05) :793-799

[7] New four-component reactions in water: a convergent approach to the metal-free synthesis of spiro[indoline/acenaphthylene-3,4′-pyrazolo[3,4-b]pyridine derivatives [J].

Balarnurugan, Kamaraj ;

Perumal, Subbu ;

Menendez, J. Carlos .

TETRAHEDRON, 2011, 67 (18) :3201-3208

[8] Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters [J].

Cao, Yiming ;

Jiang, Xianxing ;

Liu, Luping ;

Shen, Fangfang ;

Zhang, Futing ;

Wang, Rui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9124-9127

[9] 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

[10] Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].

Chen, Qiong ;

Zhu, Xiao-Lei ;

Jiang, Li-Li ;

Liu, Zu-Ming ;

Yang, Guang-Fu .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603

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