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Synthesis 2010(10): 1593-1598  
DOI: 10.1055/s-0029-1218746
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-(2-Dialkylamino-4H-3,1-benzothiazin-4-yl)acetic Acid Derivatives and 2-(2-Thioxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetic Acid Derivatives

Shuhei Fukamachi, Hisatoshi Konishi, 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; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 5 January 2010
Publication Date:
15 April 2010 (online)

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Abstract

An efficient method for the preparation of 2-(4H-3,1-benzothiazin-4-yl)acetic acid derivatives and 2-(2-thioxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetic acid derivatives has been developed. The reaction of 3-(2-isothiocyanatophenyl)propenoic acid derivatives with secondary amines in methanol at room temperature gave the corresponding thiourea intermediates, which on heating at reflux temperature cyclized by an attack of the sulfur atom on the propenoic moiety in a 1,4-addition manner, to give 2-(2-dialkylamino-4H-3,1-benzothiazin-4-yl)acetic acid derivatives in one pot. A similar sequence using primary amines in place of secondary amines afforded 2-[3-alkyl(or aryl)-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-yl]acetic acid derivatives.

Key words

4H-3,1-benzothiazines - 2-thioxo-1,2,3,4-tetrahydroquinazolines - 3-(2-isothiocyanatophenyl)propenoic acids - thioureas - 1,4-addition

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