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Short Paper | Regular issue | Vol 85, No. 12, 2012, pp.3007-3013
Published online, 30th October, 2012
DOI: 10.3987/COM-12-12584
One-Pot Synthesis of 2-(1,4-Dihydro-2H-3,1-benzothiazin-2-ylidene)propanedioic Acid Derivatives by the Reaction of 2-(1-Bromoalkyl)phenyl Isothiocyanates with Propanedioic Acid Derivatives Using Sodium Hydride

Kazuhiro Kobayashi* and Kosuke Ezaki

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


An efficient one-pot procedure for the preparation of 2-(1,4-dihydro-2H-3,1-benzothiazin-2-ylidene)propanedioic acid derivatives from 2-(1-bromoalkyl)phenyl isothiocyanates with propanedioic (malonic) acid derivatives, such as propanedinitrile, ethyl cyanoacetates, 3-oxo-3-(pyrrolidin-1- yl)propanenitrile and diethyl propanedioate, has been developed. The reactions are carried out in the presence of two equivalents of sodium hydride at –20 ˚C to give the desired products.