杂环稠合的1,3-恶嗪-6-酮的无痕固相合成

Traceless solid-phase synthesis of heteroannulated 1,3-oxazin-6-ones.

作者信息

Che Jun, Raghavendra Makam S, Lam Yulin

机构信息

Department of Chemistry, National University of Singapore, Singapore.

出版信息

J Comb Chem. 2009 May-Jun;11(3):378-84. doi: 10.1021/cc800193r.

DOI:10.1021/cc800193r

PMID:19334684

Abstract

A microwave-assisted solid-phase synthesis of heteroannulated 1,3-oxazin-6-ones has been developed. Significant rate enhancement was observed for all steps carried out under microwave irradiation, and the overall reaction time was dramatically shortened when compared to the conventional procedures. A representative set of 20 bi- and tricyclic heteroannulated 1,3-oxazin-6-ones was prepared. Key steps in the synthesis are (i) five-member heterocycle formation, (ii) acylation of amine, and (iii) ring closure to give the heteroannulated 1,3-oxazin-6-one.

摘要

已开发出一种微波辅助的固相合成稠杂环1,3-恶嗪-6-酮的方法。在微波辐射下进行的所有步骤均观察到显著的速率提高，与传统方法相比，总反应时间大幅缩短。制备了一组具有代表性的20种双环和三环稠杂环1,3-恶嗪-6-酮。合成中的关键步骤包括：（i）五元杂环的形成；（ii）胺的酰化；（iii）闭环生成稠杂环1,3-恶嗪-6-酮。