A one-pot synthesis of 4-aryl-2-methyl-1,2,3,4-tetrahydro-γ-carbolines from 5-aryloxazolidines and indoles via a Mannich/Friedel-Crafts sequence

被引：15

作者：

Moshkin, Vladimir S. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci, Dept Chem, Ekaterinburg 620000, Russia

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 44期

基金：

俄罗斯科学基金会;

关键词：

5-Aryloxazolidines; Indoles; 1,2,3,4-Tetrahydro-gamma-carbolines; Phenylethanolamines; Benzaldehydes; Nonstabilized azomethine ylides; DERIVATIVES; CARBOLINES; GAMMA; CYCLIZATION;

D O I：

10.1016/j.tetlet.2014.09.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzaldehydes react smoothly with the nonstabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines, which undergo ring-opening to give 2-(indol-3-ylmethylamino)-1-arylethanols in 69-79% yields on reaction with indoles in acetic acid. Their subsequent acid-catalyzed cyclization into 4-aryl-2-methyl-1,2,3,4-tetrahydro-gamma-carbolines was performed in polyphosphoric acid in moderate yields. The latter can also be prepared directly from 5-aryloxazolidines and indoles in polyphosphoric acid. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6121 / 6124

页数：4

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