Synthesis of spirocyclic 3H-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles

被引：8

作者：

Khaidarov, Adel R. ^{[1
]}

Rostovskii, Nikolai V. ^{[1
]}

Starova, Galina L. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, 7-9 Univ Embankment, St Petersburg 199034, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2018年 / 54卷 / 10期

基金：

俄罗斯基础研究基金会;

关键词：

2H-azirines; diazo compounds; pyrazines; pyrroles; spiro compounds; 1,2,3-triazoles; catalysis; RING-EXPANSION; CYCLOADDITION; ROUTE;

D O I：

10.1007/s10593-018-2378-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first derivatives of 3H-pyrrol-4-amines spiro-fused with fluorene or anthrone were synthesized in a Rh-2(OAc)(4)-catalyzed reaction of 1-sulfonyl-1,2,3-triazoles with 2H-azirines. The reaction proceeds through 1,4-diazahexa-1,3,5-triene intermediates, which under the conditions employed cyclize to stable at room temperature 1,2-dihydropyrazines. At elevated temperatures, 1,2-dihydropyrazines are in ring-chain equilibrium with 1,4-diazahexa-1,3,5-trienes, which undergo irreversible 5-exo-trig cyclization, leading to spirocyclic derivatives of 3H-pyrrol-4-amine.

引用

页码：946 / 950

页数：5

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