Author:
King J. F.,Hawson Anne,Huston B. L.,Danks L. J.,Komery J.
Abstract
Chlorination of 2H-1,2,3-benzothiadiazine 1,1-dioxide(1) in wet methylene chloride gives o-formylbenzenesulfonyl chloride (4), but in dry methylene chloride at 0° yields the chlorosultine 3-chloro-3H-2,1-benzoxathiole 1-oxide (2); the latter is readily hydrolyzed to the "pseudo-acid" 3H-2,1-benzoxathiol-3-ol 1-oxide (3) which on further chlorination forms 4. In 1,2-dichloroethane at −20° chlorination of 1 gave the "coupled product" 14, whereas in dimethylformamide at room temperature the cyclic acyl chloride hydrazone 4-chloro-2H-1,2,3-benzothiadiazine was isolated in poor yield. The acyl chloride hydrazones (16) were the products obtained following chlorination of some representative aromatic acyclic tosylhydrazones (15). 3H-2,3,4-Benzothiadiazepine2,2-dioxide (19), a previously unknown heterocyclic system, was synthesized in two steps from 1,3-dihydrobenzo[c]thiophene (17). Chlorinolysis of 19 gave o-chloromethylbenzal chloride (21). These reactions are believed to involve formation of the α-chloroazo compound (e.g. 22) as the first step. The formation of 2 from 1 is discussed in terms of three possible routes, two which involve the sulfene 23.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
45 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. Practical Synthesis of Variously Substituted 2,3,4-Benzothiadiazepine 2,2-Dioxides;Synthesis;2022-03-14
2. Synthesis and Chemistry of 1,2,3-Benzothiadiazine 1,1-Dioxide Derivatives: A Comprehensive Overview;Chemistry;2020-07-21
3. Synthesis of 2,5-dihydroimidazo[4,5-e][1,2,3]thiadiazine 1,1-dioxides—Derivatives of a novel heterocyclic system;Russian Journal of Organic Chemistry;2017-12
4. Thermal Ring Contraction Reactions of 9-Aryl-5H,7H-[1,2,5]thiadiazolo[3,4-h][2,3,4]benzothiadiazepine 6,6-Dioxides. Experimental and Computational Studies for Understanding the Course of the Transformations;The Journal of Organic Chemistry;2017-02-01
5. Consecutive alkylation–reduction reactions of 2 H -1,2,3-benzothiadiazine 1,1-dioxide derivatives. Synthesis of 2-alkyl-, 3-alkyl-, and 2,3-dialkyl-3,4-dihydro-2 H -1,2,3-benzothiadiazine 1,1-dioxides;Tetrahedron;2015-01