Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE): Rapid access to the diarene-fused 1,4,7-triazecine ring system

被引：11

作者：

Grintsevich, Sergey ^{[1
]}

Sapegin, Alexander ^{[1
]}

Reutskaya, Elena ^{[1
]}

Krasavin, Mikhail ^{[1
]}

机构：

[1] St Petersburg State Univ, St Petersburg 199034, Russia

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

Medium-sized rings; 1,4,7-triazecines; 1.4]diazepines; Hydrated imidazoline ring expansion; Nevirapine; LACTAMS;

D O I：

10.1016/j.tetlet.2018.11.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：20 / 22

页数：3

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