DIELS-ALDER REACTIVITY OF PYRANO[4,3-B]INDOL-3-ONES, INDOLE 2,3-QUINODIMETHANE ANALOGS

被引：57

作者：

MOODY, CJ ^{[1
]}

RAHIMTOOLA, KF ^{[1
]}

机构：

[1] IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 03期

关键词：

D O I：

10.1039/p19900000673

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pyrano[4,3-b]indol-3-ones (7) are stable indole-2,3-quinodimethane type dienes, which undergo Diels-Alder reaction with alkynes to give, after loss of carbon dioxide, carbazoles. The reactivity of the diene is increased by the presence of the electron-withdrawing t-butoxycarbonyl group on the indole nitrogen. The pyranoindolones (7) are less reactive, and exhibit the opposite regiochemistry in their Diels-Alder reactions than the isomeric pyrano[3,4-b]indol-3-ones (1). Factors which affect the regiochemistry of the Diels-Alder reaction are discussed.

引用

页码：673 / 679

页数：7

共 16 条

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