118134-11-5Relevant articles and documents
Nitrile Sulphides. Part 7. Synthesis of Benzopyranoisothiazoles and Isothiazoloquinolines
Brownsort, Peter A.,Paton, Michael
, p. 2339 - 2344 (2007/10/02)
o-Hydroxybenzonitrile sulphide (1a), generated by thermal decarboxylation of the corresponding 1,3,4-oxathiazol-2-one, reacts with dimethyl acetylenedicarboxylate to afford methyl 4-oxo-4H-benzopyranoisothiazole-3-carboxylate (6a), from which the parent ring system (6c) can be prepared by hydrolysis and decarboxylation.The same products are formed from the acetoxy analogue (1b) via hydrolysis of isothiazole (5b). o-Acetamidobenzonitrile sulphide (1c) reacts similarly forming isothiazole (5c) and subsequently isothiazoloquinolin-4(5H)-one (7c) by hydrolysis, ring closure, and decarboxylation.Cycloadditions to ethyl cyanoformate, ethyl propiolate, and diethyl fumarate have also been examined.