Author:
Birchall G. R.,Rees A. H.
Abstract
We have investigated the ring expansion of some substituted 1,4-naphthoquinones by hydrazoic acid to yield new 1-benzazepine derivatives of the "azatropolone" type. Ring contraction of those products, which are 2,5-dihydro-3-hydroxy-2,5-dioxo-1-benzazepines, gives 4-quinolone-2-carboxylic acids. Some of the reactions of the new benzazepine system were investigated. Attempts to prepare substituted derivatives suitable for making 1-benzazatrop-5-one were not successful.The effect of substituents on the ring expansion reaction is discussed and an anomalous ring expansion to a 2,5-dihydro-4-hydroxy-2,5-dioxo-1-benzazepine is described and explained mechanistically.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
18 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献
1. Azepine Ring Systems Containing two Rings;Chemistry of Heterocyclic Compounds: A Series Of Monographs;2008-01-02
2. Synthesis of the Quinoline Ring System;Chemistry of Heterocyclic Compounds: A Series Of Monographs;2008-01-02
3. Analogs of 3-Hydroxy-1H-1-benzazepine-2,5-dione: Structure−Activity Relationship at N-Methyl-d-aspartate Receptor Glycine Sites;Journal of Medicinal Chemistry;1996-01-01
4. References to Volume 3;Comprehensive Organic Functional Group Transformations;1995
5. Alkyl Chalcogenides: Oxygen-based Functional Groups;Comprehensive Organic Functional Group Transformations;1995