Reactions of o-aminothiophenol and o-aminophenyl disulfide with itaconic anhydride and (-)-dimenthyl itaconate: Access to enantiomerically pure 1, 5- …

MM Baag, MK Sahoo, VG Puranik, NP Argade

Index: Baag, Md. Merajuddin; Sahoo, Manoj Kumar; Puranik, Vedavati G.; Argade, Narshinha P. Synthesis, 2007 , # 3 p. 457 - 463

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Citation Number: 8

Abstract

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 ...