A novel one-pot three-component reaction:: Synthesis of triheterocyclic 4H-pyrimido[2,1-b]benzazoles ring systems

被引：147

作者：

Shaabani, A ^{[1
]}

Rahmati, A ^{[1
]}

Naderi, S ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Dept Chem, Tehran, Iran

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 24期

关键词：

multicomponent; 2-aminobenzimidazole; 2-aminobenzo-thiazole; 4H-pyrimido[2,1-b]benzothiazoles; 4H-pyrimido[2,1-b]benzimidazoles;

D O I：

10.1016/j.bmcl.2005.08.101

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel one-pot three-component condensation reaction of an aldehyde, beta-ketoester and 2-aminobenzimidazole or 2-aminobenzothiazole in 1,1,3,3-N,N,N',N'-tetramethylguanidinium trifluoroacetate as an ionic liquid is described. During the course of this reaction 4H-pyrimido[2,1-b]benzimidazoles or 4H-pyrimido[2,1-b]benzothiazoles are formed in high yields at 100 degrees C. The ionic liquid can be recovered conveniently and reused efficiently. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5553 / 5557

页数：5

共 37 条

[1] Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses
Abelman, MM
Smith, SC
James, DR
[J]. TETRAHEDRON LETTERS, 2003, 44 (24) : 4559 - 4562
[2] SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED 1,4-DIHYDROPYRIDINES AND ANALOGOUS CALCIUM-ANTAGONISTS BY MICROWAVE-HEATING
ALAJARIN, R
JORDAN, P
VAQUERO, JJ
ALVAREZBUILLA, J
[J]. SYNTHESIS-STUTTGART, 1995, (04): : 389 - 391
[3] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS 51 - BICYCLIC DIHYDROPYRIMIDINES AS POTENT MIMICS OF DIHYDROPYRIDINES
ATWAL, KS
MORELAND, S
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (06) : 291 - 294
[4] ATWAL KS, 1988, Patent No. 254119
[5] Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[6] BOROVIK VP, 1970, KHIM FARM ZH+, V4, P32
[7] New regioselective multicomponent reaction: One pot synthesis of spiro heterobicyclic aliphatic rings
Byk, G
Gottlieb, HE
Herscovici, J
Mirkin, F
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (06): : 732 - 735
[8] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[9] 2-U
[10] KAPPE CO, 1993, TETRAHEDRON, V49, P6937

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