New simple synthesis of ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thiones: Direct formation from carbon disulfide and (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles

Qiuping Ding; Yuqing Lin; Guangni Ding; Fumin Liao; Xiaoyan Sang; Yi-Yuan Peng

doi:10.3762/bjoc.9.49

New simple synthesis of ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thiones: Direct formation from carbon disulfide and (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles

Beilstein J Org Chem. 2013:9:460-6. doi: 10.3762/bjoc.9.49. Epub 2013 Mar 1.

Authors

Qiuping Ding¹, Yuqing Lin, Guangni Ding, Fumin Liao, Xiaoyan Sang, Yi-Yuan Peng

Affiliation

¹ Key Laboratory of Functional Small Organic Molecules, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.

Abstract

A new simple and efficient method to construct ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thione derivatives has been developed from carbon disulfide and (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles under mild conditions, without the need for a metal catalyst. The newly developed method tolerates a wide range of substrates in moderate to excellent yields. Moreover, this method is advantageous over previous ones for the easy synthesis of reactants.

Keywords: (E)-3-(2-aminoaryl)acrylate; (E)-3-(2-aminoaryl)acrylonitrile; 4H-3,1-benzothiazine-2-thione; Michael addition; carbon disulfide.