Synthesis of 3-(1,2-dioxoethyl)- and 2,3-dicarbonyl-containing pyrroles

被引：27

作者：

Galenko, Alexey V. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Avdontceva, Margarita S. ^{[2
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 198504, Russia

[2] St Petersburg State Univ, Inst Earth Sci, St Petersburg 199034, Russia

来源：

TETRAHEDRON | 2015年 / 71卷 / 13期

基金：

俄罗斯基础研究基金会;

关键词：

Pyrrole; Azirine; Cyclocondensation; Metal catalysis; STRUCTURAL-CHARACTERIZATION; BIOLOGICAL EVALUATION; DOMINO REACTION; VINYL AZIDES; 2H-AZIRINES; AZIRINES; ESTERS; ACID; 2-PHENYLAZIRINE; ISOMERIZATION;

D O I：

10.1016/j.tet.2015.02.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transition metal-catalyzed reaction of 2H-azirines with 1,2,4-tricarbonyl compounds leads to 3-(1,2-dioxoethyl)- and 2,3-dicarbonyl-pyrrole derivatives, useful building blocks for the preparation of 3-heterocyclyl pyrroles and pyrroles fused with heterocycles. The influence of catalysts and the reaction conditions on the yields of pyrroles and the regioselectivity of the reaction were studied. Experimental and theoretical results suggest that the reaction proceeds via the formation of an intermediate azirine metal complex and subsequent nucleophilic N-C-3 bond cleavage. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1940 / 1951

页数：12

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