ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Aldol condensation of 2-methylbenzothiazole and 2-cyanomethylbenzothiazole with dicarboxylic-acids anhydrides

M. Lácová and P. Chabreček

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, CS-84215 Bratislava

Abstract: By the Perkin synthesis of 2-methyl- and 2-cyanomethylbenzothiazole with phthalic anhydride or its 3- or 4-nitro derivatives the corresponding phthalides or 1,3-indandiones were prepared. 2-Cyanomethylbenzothiazole reacts with maleic anhydride in acetic anhydride to yield 4-[2-benzothiazolyl(cyano)methylene]-4-butenolide; in benzene these reactants afforded 5-(2-benzothiazolyl)-5-cyano-4-oxo-2-pentenoic acid. Treatment of the phthalides with hydrazine or Phenylhydrazine led to l-oxo-2-R-4-(2-benzothiazolylmethyl)-1,2-dihydrophthalazines.

Full paper in Portable Document Format: 415a709.pdf

Chemical Papers 41 (5) 709–717 (1987)