INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - REACTIONS WITH 1,2,4-TRIAZINES AND 1,2-DIAZINES

被引：90

作者：

BENSON, SC ^{[1
]}

GROSS, JL ^{[1
]}

SNYDER, JK ^{[1
]}

机构：

[1] BOSTON UNIV,DEPT CHEM,590 COMMONWEALTH AVE,BOSTON,MA 02215

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indole reacts with 1,2,4-triazines in the absence of solvent or in the presence of limited amounts of solvent to produce β- or γ-carbolines, benzo[f][l,7]naphthyridines, or the noncyclized 3-[5-(l,2,4-triazinyl)]indoles. The combined yield of cycloadducts with tricarbalkoxytriazines exceeds 90%, with the production of γ-carbolines exceeding 80%. the regiochemistry of the adduct and the ratio of the products is determined mainly by electronic effects of the triazine substituents. Indole also undergoes a cyclocondensation reaction with tetramethyl 1,2-diazine-3,4,5,6-tetracarboxylate to give trimethyl 5H-6-oxophenanthridine-2,3,4-tricarboxylate. © 1990, American Chemical Society. All rights reserved.

引用

页码：3257 / 3269

页数：13

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