Synthesis of Novel Spiro Pyrrolidine and Pyrrolizine Derivatives by 1,3-Dipolar Cycloaddition

被引：8

作者：

Li Xiaofang ^{[1
,2
]}

Zheng Aiting ^{[1
]}

Liu Bin ^{[1
]}

Yu Xianyong ^{[1
]}

Yi Pinggui ^{[1
]}

机构：

[1] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Hunan Prov Coll Key Lab QSAR QSPR, Key Lab Theoret Chem & Mol Simulat,Minist Educ, Xiangtan 411201, Hunan, Peoples R China

[2] Tianjin Univ, Sch Chem Engn & Technol, Tianjin 300072, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2010年 / 28卷 / 07期

基金：

中国国家自然科学基金;

关键词：

spiroheterocycle; 1,3-dipolar cycloaddition; azomethine ylides; dihydroimidazo[2,1-b]thiazol-3(2H)-one; STEREOSELECTIVE-SYNTHESIS; SPIROPYRROLIZIDINES; SPIROTRYPROSTATIN; DISCOVERY; SYSTEMS; AGENTS;

D O I：

10.1002/cjoc.201090209

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,3-dipolar cycloaddition of azomethine ylides derived from isatin and amino acids viz. sarcosine and proline to 2-arylmethylidene-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-ones afforded novel spiro pyrrolidines and pyrrolizidines regio- and stereoselectively in moderate yields. The products were characterized thoroughly by IR, MS, NMR together with elementary analysis.

引用

页码：1207 / 1211

页数：5

共 22 条

[1] Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1351-1358

[2] POTENTIAL ANTI-TUMOR AGENTS .16. IMIDAZO[2,1-B]THIAZOLES [J].

ANDREANI, A ;

RAMBALDI, M ;

ANDREANI, F ;

BOSSA, R ;

GALATULAS, I .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1988, 23 (04) :385-389

[3]

Andreani A, 1995, Pharm Acta Helv, V70, P325, DOI 10.1016/0031-6865(95)00038-0

[4] SYNTHESIS AND CARDIOTONIC ACTIVITY OF 2,5-DIMETHOXYPHENYLIMIDAZO[2,1-B]THIAZOLES [J].

ANDREANI, A ;

RAMBALDI, M ;

LOCATELLI, A ;

BOSSA, R ;

GALATULAS, I ;

NINCI, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (04) :431-433

[5] 6-thienyl and 6-phenylimidazo[2,1-b]thiazoles as inhibitors of mitochondrial NADH dehydrogenase [J].

Andreani, A ;

Rambaldi, M ;

Leoni, A ;

Morigi, R ;

Locatelli, A ;

Giorgi, G ;

Lenaz, G ;

Ghelli, A ;

Degli Esposti, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (10) :883-889

[6] An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides [J].

Babu, A. R. Suresh ;

Raghunathan, R. .

TETRAHEDRON LETTERS, 2008, 49 (31) :4618-4620

[7] Synthesis of [1,3]dithiole and spiro[1,3]dithiole thiopyran derivatives of the [1,2]dithiolo[1,4]thiazine ring system [J].

Barriga, S ;

Fuertes, P ;

Marcos, CF ;

Rakitin, OA ;

Torroba, T .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6439-6448

[8] Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted α-methylene-γ-lactones [J].

Castulík, J ;

Marek, J ;

Mazal, C .

TETRAHEDRON, 2001, 57 (39) :8339-8347

[9] Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835

[10] Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues [J].

Edmondson, S ;

Danishefsky, SJ ;

Sepp-Lorenzino, L ;

Rosen, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2147-2155

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