A study of the reaction of 2-thiazolin-4-ones with some electrophiles under microwave irradiation versus conventional condition

Coupling of 5-dimethylaminomethylene-3-methyl-2-(pyridine-2-ylimino)-thiazolidin-4- one (3) with diazotized methyl anthranilate afforded the 3-methyl-5-(2- methoxycarbonylphenylhydrazono)- 2-pyridine-2-ylimino)thiazolidin-4-one (5). reaction of 2-(arylamino)thiazol-4-ones 1a,b with arylidenemalononitriles under microwave irradiation gave 2-substituted amino-5- arylidenethiazolin- 4-ones 9a–f. alternatively, compound 9 could also be obtained by reacting compound 1 with aromatic aldehydes. treatment of compound 9 with acetic acid yielded the corresponding thiazolin-2,4-diones 10. however, the reaction of 1 with cyanoacetic acid yielded the corresponding 4-cyanoacetyl derivative 12, in good yield. the ^1h, ^13c nmr spectra of some representative products and x-ray crystal structure determination are discussed.