Regioselective anionic [3+2] cyclizations of isoxazole, pyrazole and 1,2,4-triazole dinucleophiles -: Efficient synthesis of 2,4-dihydroimidazo-[4,5-b]quinoxalines, 3H-imidazo[1,2-b]pyrazoles and 5H-imidazo[2,1-c][1,2,4]triazoles

被引：0

作者：

Langer, P

Wuckelt, J

Döring, M

Schreiner, PR

Görls, H

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

[2] Univ Jena, Inst Anorgan & Analy Chem, D-07743 Jena, Germany

[3] Univ Georgia, Dept Chem, Athens, GA 30602 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 2001卷 / 12期

关键词：

carbanions; domino reactions; nitrogen heterocycles; regioselectivity; cyclizations;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective cyclization reactions between oxaldiimidoyl dichlorides and 3-aminopyrazole and 3-amino-1,2,4-triazole provide convenient access to biologically relevant 3H-imidazo[1,2-b]pyrazoles and a 5H-imidazo[2,1-c][1,2,4]triazole. In contrast, treatment of 3-aminoisoxazoles with diimidoyl dichlorides results in a new and efficient anionic domino process for the synthesis of biologically relevant 2,4-dihydro-1H-imidazo[4,5-b]quinoxalines. All cyclizations proceed with high regioselectivities, which are explained with the aid of semiempirical computations.

引用

页码：2257 / 2263

页数：7

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