BASE-INDUCED CYCLOADDITION OF TOSYLMETHYL OR (TERT-BUTOXYCARBONYL)METHYL ISOCYANIDE TO 1,4-DISUBSTITUTED 2,3-DINITRO-1,3-BUTADIENES - ACCESS TO 2,3-DISUBSTITUTED 4-ETHYNYLPYRROLES

被引：21

作者：

DELLERBA, C

GIGLIO, A

MUGNOLI, A

NOVI, M

PETRILLO, G

STAGNARO, P

机构：

[1] CNR,IST CHIM ORGAN,CTR STUDIO CHIM COMPOSTI CICLOALIFATICI & AROMATI,I-16132 GENOA,ITALY

[2] IST CHIM FIS,I-16132 GENOA,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 17期

关键词：

D O I：

10.1016/0040-4020(95)98713-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 1,4-disubstituted 23-dinitro-1,3-butadienes 1a-g in THF with isocyanides XCH(2)NC (TosMIC, X = tosyl; TBICA, X = COOBu(t)) and DBU furnish good to moderate yields of 2,3-disubstituted 4- ethynylpyrroles 5a-g or 6a-g. In the reaction of Ig with TosMIC and DBU the nitrovinyl pyrrole 7g and the 3,3'-dipyrrole 4g are also isolated as by-products. A mechanism involving sequential base-induced addition, elimination and cyclization steps is advanced to account for the formation of the isolated products.

引用

页码：5181 / 5192

页数：12