Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines

被引：23

作者：

Miyata, O

Takeda, N

Kimura, Y

Takemoto, Y

Tohnai, N

Miyata, M

Naito, T ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[3] Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 15期

基金：

日本学术振兴会;

关键词：

3,3]-sigmatropic rearrangement; N-trifluoroacetyl cnehydrazines; indole; indoline; dienylimine;

D O I：

10.1016/j.tet.2006.01.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3629 / 3647

页数：19

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