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

Abstract EN

Coupling of 5-dimethylaminomethylene-3-methyl-2-(pyridine-2-ylimino)-thiazolidin-4-one (3) with diazotized methyl anthranilate afforded the 3-methyl-5-(2 methoxycarbonylphenylhyd-razono)-2-pyridine-2-ylimino) thiazolidin-4-one (5).

Reaction of 2-(aryl amino) thiazol-4-ones la, b with arylidenemalononitriles under microwave irradiation gave 2-substituted amino-5-arylidene-thiazolin-4-ones 9 a-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 'H, 13C NMR spectra of some representative products and X-ray crystal structure determination are discussed.