Reaction of benzothiazole and substituted benzothiazoles with dimethyl acetylenedicarboxylate. A novel heterocyclic ring transformation

A McKillop, TSB Sayer…

Index: McKillop,A. et al. Journal of Organic Chemistry, 1976 , vol. 41, # 8 p. 1328 - 1331

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Citation Number: 7

Abstract

The reactions of benzothiazole 1 with dimethyl acety- lenedicarboxylate (DMAD) have been studied by various groups of workers during the last 12 years, but only recent- ly have the structures of the various products been unam- biguously assigned by Ogura and his colleagues.2 At least three products can be obtained, depending on the nature of the solvent used; thus, 2 and 3 are formed in 5 and 8% yield, respectively, when methanol is employed, whereas 4 is ...