Synthesis 2012; 44(19): 3019-3026
DOI: 10.1055/s-0032-1316769
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Aryl-4-methyl- and 4,4-Dimethyl-4H-pyrrolo[2,1-c][1,4]benzothiazines by an Easy Five-Step Sequence Starting from 2-Sulfanylbenzenamines

Kazuhiro Kobayashi*
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: +81(857)315263   Email: kkoba@chem.tottori-u.ac.jp
,
Akane Hyota
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: +81(857)315263   Email: kkoba@chem.tottori-u.ac.jp
,
Hideaki Kondo
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: +81(857)315263   Email: kkoba@chem.tottori-u.ac.jp
,
Ayumi Imaoka
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan, Fax: +81(857)315263   Email: kkoba@chem.tottori-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 26 June 2012

Accepted after revision: 23 July 2012

Publication Date:
21 August 2012 (online)


Abstract

A convenient process for the synthesis of 4-aryl-4-methyl- and 4,4-dimethyl-4H-pyrrolo[2,1-c][1,4]benzothiazines has been developed. Cyclization of 1-{2-[1-aryl(or methyl)ethenylsulfanyl]phenyl}pyrroles, which are readily obtained by an easy four-step sequence starting from commercially available 2-sulfanylbenzenamines, to the desired heterocycles can be effected in good to excellent yields on treatment with a catalytic amount of hydriodic acid.