Reactions of o-Aminothiophenol and o-Aminophenyl Disulfide with Itaconic Anhydride and (-)-Dimenthyl Itaconate: Access to Enantiomerically Pure 1,5-Benzothiazepines and Benzothiazolyl-2-methylacrylic Acid

Md Merajuddin Baag; Manoj Kumar Sahoo; Vedavati G. Puranik; Narshinha P. Argade

doi:10.1055/s-2006-958977

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Synthesis 2007(3): 457-463
DOI: 10.1055/s-2006-958977

PAPER

Reactions of o-Aminothiophenol and o -Aminophenyl Disulfide with Itaconic Anhydride and (-)-Dimenthyl Itaconate: Access to Enantiomerically Pure 1,5-Benzothiazepines and Benzothiazolyl-2-methylacrylic Acid [1]

Md. Merajuddin Baag^a, Manoj Kumar Sahoo^a, Vedavati G. Puranik^b, Narshinha P. Argade*^a
^a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
^b Centre for Material Characterization, National Chemical Laboratory, Pune 411 008, India
e-Mail: np.argade@ncl.res.in;

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Publication History

Received 6 October 2006
Publication Date:
08 January 2007 (online)

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Abstract

A facile chemo- and regioselective reactions of o-aminothiophenol (o-ATP) with itaconic anhydride is described. 1,5-Benzothiazepinyl-3-acetic acid is obtained in 81% yield via the exclusive Michael type addition of the thiol unit from o-ATP to the carbon-carbon double bond in itaconic anhydride followed by an intramolecular anhydride ring opening with an amine unit. The moderately stereoselective Michael type addition of the thiol unit from o-ATP to (-)-dimenthyl itaconate to obtain a mixture of diastereomers in a 7:3 ratio in 82% yield has been demonstrated. The reductive sulfur-sulfur bond cleavage in the dicarboxylic acid, 2-({2-[2-(3-carboxybut-3-enoylamino)phenyldisulfanyl]phenylcarbamoyl}methyl)acrylic acid, to the corresponding benzothiazolyl-2-methylacrylic acid in 84% yield, instead of the desired benzothioazocine is also reported.

Key words

o-aminothiophenol - itaconic anhydride - dimenthyl itaconate - chemo- - regio- and stereoselective reactions - benzothiazepines - benzothiazoles - synthesis

1

NCL Communication No. 6697.

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1

NCL Communication No. 6697.

10

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 600537 and 600538. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].