Facile one pot synthesis of 8-chloro-[1,2,4]triazolo[4,3-a]pyrazines via oxidative cyclisation using chloramine T

被引：11

作者：

Mal, Sanjib ^{[1
]}

Prathap, Kilaru Jagadeesh ^{[1
]}

Smith, Stephen C. ^{[2
]}

Umarye, Jayant D. ^{[1
]}

机构：

[1] Syngenta Biosci Pvt Ltd, Santa Monica Works, Ilhas 403110, Goa, India

[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 22期

关键词：

Fused nitrogen heterocycles; Oxidative cyclisation; Chloramine T; Intramolecular reaction; One pot synthesis; MEDIATED SYNTHESIS; 1,2,4-TRIAZOLES; PYRIDINE; SERIES;

D O I：

10.1016/j.tetlet.2015.04.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and expedient one pot synthesis of 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine derivatives from 2-chloro-3-hydrazinylpyrazine and aldehydes is described using chloramine T trihydrate as a safe and convenient electrocyclisation (oxidising) agent. The presence of the chloro group on pyrazine enabled us to access versatile new synthetic scaffolds by easy diversification using palladium catalysed Suzuki-Miyaura and Sonogashira cross coupling reactions. The products are obtained in high yields in short reaction time under mild conditions without the need for chromatographic purification. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2896 / 2901

页数：6

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