DIELS-ALDER REACTIONS OF METHYL-SUBSTITUTED AND PI-ACCEPTOR-SUBSTITUTED 2-VINYL-INDOLES WITH DIMETHYL ACETYLENEDICARBOXYLATE AND TETRACYANOETHYLENE - NOVEL FUNCTIONALIZED CARBAZOLES

被引：10

作者：

PINDUR, U ^{[1
]}

EITEL, M ^{[1
]}

机构：

[1] UNIV MAINZ,DEPT CHEM & PHARM,W-6500 MAINZ 1,GERMANY

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 04期

关键词：

D O I：

10.1002/jhet.5570280419

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reactions of the 2-vinylindoles 1a-1d, which are now readily accessible, with dimethyl acetylenedicarboxylate and tetracyanoethylene give rise to the novel 1,2-dihydro- and 1,2,3,4-tetrahydrocarbazoles 2, 4, and 5 as well as the fully aromatized carbazoles 3. With regard to the product spectrum, the mechanistic rationale comprises a Diels-Alder step, formal 1,3-hydrogen shift, ene reaction, and dehydrogenation. Conformational aspects of the 1,2-dihydrocarbazoles 2b and 2c are also discussed.

引用

页码：951 / 954

页数：4

共 20 条

[1]

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[2]

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[3]

EITEL M, 1989, SYNTHESIS-STUTTGART, P364

[4]

EITEL M, 1990, THESIS U MAINZ FRG