2-芳基-N-对甲苯磺酰氮杂环丁烷作为与腈发生[4+2]环加成反应的形式1,4-偶极子：一种简便合成四氢嘧啶衍生物的方法。

2-aryl-N-tosylazetidines as formal 1,4-dipoles for [4 + 2] cycloaddition reactions with nitriles: an easy access to the tetrahydropyrimidine derivatives.

作者信息

Prasad B A Bhanu, Bisai Alakesh, Singh Vinod K

机构信息

Department of Chemistry, Indian Institute of Technology, Kanpur, 208 016, India.

出版信息

Org Lett. 2004 Dec 23;6(26):4829-31. doi: 10.1021/ol048161l.

DOI:10.1021/ol048161l

PMID:15606077

Abstract

[reaction: see text] A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitriles in the presence of BF3.OEt2 has been described for the synthesis of substituted tetrahydropyrimidines. It is proposed that the reaction proceeds in Ritter fashion.

摘要

[反应：见正文] 已经开发出一种从N-甲苯磺酰基芳基亚胺开始的两步合成2-芳基-N-甲苯磺酰基氮杂环丁烷的新路线，总产率为63-70%。已经描述了在BF3·OEt2存在下，这些2-芳基-N-甲苯磺酰基氮杂环丁烷与腈进行形式上的[4+2]环加成反应以合成取代的四氢嘧啶。有人提出该反应以里特反应方式进行。