Highly efficient one-pot synthesis of 1-substituted-1,2,3,4-tetrahydropyrazino[1,2-a]indoles

被引：32

作者：

Tiwari, RK ^{[1
]}

Singh, J ^{[1
]}

Singh, D ^{[1
]}

Verma, AK ^{[1
]}

Chandra, R ^{[1
]}

机构：

[1] Univ Delhi, Dr BR Ambedkar Ctr Biomed Res, Synth Organ Chem Res Lab, Delhi 110007, India

来源：

TETRAHEDRON | 2005年 / 61卷 / 40期

关键词：

intramolecular cyclization; benzotriazole; Lewis acid; frontier molecular orbital;

D O I：

10.1016/j.tet.2005.07.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and general one-pot synthesis of 1-substituted-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles is described. The approach uses 2-(3-methyl-1H-indol-1-yl) ethylamine, benzotriazole and aldehydes in the presence of catalytic amount of acid catalysts (AlCl3, ZnCl2, ZnBr2, p-TsOH, CH3SO3H) and proceeds in high yields via iminium cation intramolecular cyclization. The mechanism of the observed intramolecular cyclization reaction has been investigated theoretically by means of PM3 semiempirical method and results were consistent with the experimental results. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：9513 / 9518

页数：6

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