Synthesis of an Antibacterial Compound Containing a 1,4-Substituted 1H-1,2,3-Triazole: A Scaleable Alternative to the "Click" Reaction

被引：79

作者：

Hanselmann, Roger ^{[1
]}

Job, Gabriel E. ^{[1
]}

Johnson, Graham ^{[1
]}

Lou, Rongliang ^{[1
]}

Martynow, Jacek G. ^{[1
]}

Reeve, Maxwell M. ^{[1
]}

机构：

[1] Rib X Pharmaceut Inc, New Haven, CT 06511 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2010年 / 14卷 / 01期

关键词：

TERMINAL ALKYNES; 1,2,3-TRIAZOLES; REDUCTION; AMINES; AZIDES; ALCOHOLS; SOLVENTS; HEALTH; ESTERS; ION;

D O I：

10.1021/op900252a

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The copper-catalyzed "click" reaction of an azide with an alkyne has become a popular method to build tip 1,4-substituted 1H-1,2,3-triazoles in medicinal chemistry and this approach was used on a laboratory scale during the preparation of novel macrolide 1. However, the manufacture of the key azide component, as well as its subsequent use in the presence of a copper catalyst on a large scale, was associated with potential safety concerns. Therefore, a sequence was developed in which construction of the 1,4-substituted 1H-1,2,3-triazole in 1 was accomplished via cyclocondensation of an alpha,alpha-dichloro tosyl hydrazone with an amine.

引用

页码：152 / 158

页数：7

共 31 条

[21] Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A [J].