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Abstract
4-Methoxyphenylazide cycloadds to the thiono function and undergoes nucleophilic attack at other electrophilic centers of 5-benzoylmethyl-(1a) and E,Z-5-(4-bromobenzoylmethylene)-(E,Z-2b) -2-thi-oxx-4-oxo-1,3-thiazolidines in non site selective reactions to afford variety of products. With la, the attack at the thiono as well as the hetero-ring carbonyl functions leads to the 5-benzoylmethylene-2-(4-methoxyphenylimino)-derivative (3) and the ring fission product 2–4. Similar treatment of E,Z-Zb gives a mixture of the respective E,Z-2-(4-methoxyphenylimino)-derivative (E,Z-5) containing 80% of the Z-configurated isomer (Z-5) and the ring enlarged thiazinonethione derivative (6), due to the attack at the thiono and exocyclic double bond functions, respectively. Rationalizations for the above mentioned conversions are given. Structures of all products are evidenced by microanalytical and spectral data.