Novel 2H-1,3-benzoxazine ring formation by intramolecular heterocyclization of N-(α-aryloxyalkyl)imidoyl chlorides

Heterocyclic communications

article

Petro P. Onys’ko¹  Kateryna A. Zamulko¹  Olena I. Kyselyova¹  Yaroslav A. Syzonenko¹ 

[1] Institute of Organic Chemistry, National Academy of Sciences

关键词: 2H-1;    3-benzoxazines;    dichloromethylene;    imidoyl chlorides;    intramolecular cyclization;    polyfluoroalkyl;    trichloromethyl;   

DOI  :  10.1515/hc-2017-0102

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

A convenient synthetic approach to derivatives of 2-trichloromethyl and 2-dichlorometylene-2 H -1,3-benzoxazines, based on intramolecular heterocyclization of readily accessible N -(α-aryloxytrichloroethyl)imidoyl chlorides, was developed. Base induced dehydrochlorination of 4-phenyl- or 4-trifluoromethyl-2-trichloromethylbenzoxazines allows preparation of 2-dichloromethylene-1,3-benzoxazines, whereas dehydrochlorination of 4-fluoromethyl analogs under similar conditions is accompanied by formal 1,5- H -shift to afford respective 2-dichloromethyl-4-fluoromethylene-1,3-benzoxazines.

【 授权许可】

CC BY|CC BY-NC-ND