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
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