Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives

被引：18

作者：

Decker, M ^{[1
]}

Nguyen, TTT ^{[1
]}

Lehmann, J ^{[1
]}

机构：

[1] Univ Jena, Inst Pharm, Lehrstuhl Pharmazeut Med Chem, D-07743 Jena, Germany

来源：

TETRAHEDRON | 2004年 / 60卷 / 21期

关键词：

lactamization; lactones; amino acids; hydroxyatnides; tryptamines; hallocinogens;

D O I：

10.1016/j.tet.2004.03.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of lactamization of corresponding lactones was investigated by means of gas chromatography and synthesis of possible intermediates as references. Lactones react with amines via the amino acid with subsequent elimination of water to the corresponding lactams. In the first step, also hydroxyamides are in equilibrium with the lactones and amines, respectively, which are not able to form the amide though. This mechanism opens a new approach for the synthesis of N-beta-disubstituted tryptamines. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4567 / 4578

页数：12

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