Synthesis of N-acetyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles from N- and 2-(cyclopent-2-en-1-yl)anilines

被引：5

作者：

Skladchikov, D. A. ^{[1
]}

Buranbaeva, R. S. ^{[1
]}

Fatykhov, A. A. ^{[1
]}

Ivanov, S. P. ^{[1
]}

Gataullin, R. R. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Organ Chem, Ufa Res Ctr, Ufa 450054, Bashkortostan, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 48卷 / 12期

关键词：

CLAVICEPS-PASPALI STEVENS; HIGHLY-EFFICIENT; SOLAR-CELLS; HALL; DYES;

D O I：

10.1134/S1070428012120093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of 2-bromo-N-(cyclopent-2-en-1-yl)-4-methylaniline and N-(cyclopent-2-en-1-yl)-2-iodo-4,6-dimethylaniline with acetyl bromide in the presence of potassium carbonate gave mixtures of syn and anti atropisomers of the corresponding N-acetyl derivatives at ratios of 1: 1 and 3: 2 respectively. Heating of these mixtures in toluene in the presence of Pd(OAc)(2), PPh3, Et3N, and K2CO3 (KOAc) afforded mixtures of isomeric N-acetyl-7-methyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles at a ratio of 3: 1 or N-acetyl-5,7-dimethyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles at a ratio of 2: 3. N-Acetyl-3,3a,4,8b-tetrahydrocyclopenta[b]indole was found to undergo thermal isomerization into N-acetyl-1,3a,4,8btetrahydrocyclopenta[b]indole.

引用

页码：1550 / 1556

页数：7

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