One-Pot α-Amidosulfone-Mediated Variation of the Pictet-Spengler Tetrahydroisoquinoline Synthesis, Suitable for Amide-Type Substrates

被引：11

作者：

Arroyo, Francisco J. ^{[1
]}

Lopez-Alvarado, Pilar ^{[1
]}

Ganesan, A. ^{[2
]}

Carlos Menendez, J. ^{[1
]}

机构：

[1] Univ Complutense, Dept Quim Organ & Farmaceut, Fac Farm, E-28040 Madrid, Spain

[2] Univ E Anglia, Sch Pharm, Norwich NR4 7TJ, Norfolk, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 26期

关键词：

Stereoselective synthesis; Cyclization; Nitrogen heterocycles; Amides; RAPID ACCESS; CHEMISTRY; CONDENSATION; REDUCTION; SULFONES; AMINES;

D O I：

10.1002/ejoc.201402487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of Pictet-Spengler reactions from amide substrates is a challenging problem. We report here that the reaction between amide-type compounds (including carbamates, amides, ureas and diketopiperazines), aldehydes and p-toluenesulfinic acid constitutes an efficient method for the preparation of tetrahydroisoquinolines or pyrazino[2,1-b] isoquinolines. Unlike previously known methods, this one-pot Pictet-Spengler protocol avoids the need for strong Lewis or Bronsted acid catalysts.

引用

页码：5720 / 5727

页数：8

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