Synthesis of [1]benzopyrano[4,3-b]pyrrol-4(1H)-ones from N(α)-(2-oxo-2H-1-benzopyran-4-yl)Weinreb α-aminoamides

被引：23

作者：

Alberola, A ^{[1
]}

Alvaro, R ^{[1
]}

Ortega, AG ^{[1
]}

Sádaba, ML ^{[1
]}

Sañudo, MC ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47005 Valladolid, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 46期

关键词：

Knorr pyrrole synthesis; Weinreb amides; 1]benzopyrano[4,3-b]pyrrole; pyrrolizine;

D O I：

10.1016/S0040-4020(99)00802-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N(alpha)-(2-Oxo-2H-1-benzopyran-4-yl)Weinreb-alpha-aminoamides were prepared from 4-chlorocoumarin and alpha-aminoacid derivatives. Their reaction with organometallic compounds (RLi or RMgBr) and subsequent cyclization of ketones thus obtained, give [1]benzopyrano[4,3-b]pyrrol-4(1H)-ones. Starting from proline derivatives, simultaneously with the pyranone-pyrrole fusion, we establish an interesting procedure for the formation of pyrrolizines. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：13211 / 13224

页数：14

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