REGIOSELECTIVITY OF HALO- AND CHALCOGEN-INDUCED CYCLIZATION OF DIALLYLQUINAZOLIN-4-ONE
DOI:
https://doi.org/10.15421/jchemtech.v32i4.316035Keywords:
3-allyl-2-allylthioquinazolin-4-one, thiazolo[3,2-a]quinazoline, electrophilic intramolecular cyclization, regioselectivity, organohalogen compounds, organochalcogen compoundsAbstract
Objective. There is significant interest among medicinal chemists in compounds containing the quinazoline fragment due to their broad spectrum of biological activity and the need to develop new synthetic methods for these systems. Special attention is given to alkenyl and alkynyl derivatives of quinazolines, which serve as convenient models for studying electrophilic heterocyclization reactions. This study examines the effect of the electrophilic reagent’s nature on the regiochemistry of electrophilic intramolecular heterocyclization of 3-allyl-2-allylthioquinazolin-4-one. Methods. 1H and 13C NMR spectroscopy. Results. Experimental data indicate that the interaction of 3-allyl-2-allylthioquinazolin-4-one with hybrid halogen (iodine bromide) and the tetrahalides of selenium and tellurium leads to the regioselective formation of angular monohalides of 4-allyl-5-oxo-1,2,4,5-tetrahydrothiazolo[3,2-a]quinazolinium. It was noted that an excess of the electrophilic reagent does not affect the direction of halo- and chalcogen-induced heterocyclization. The interaction of 4-allyl-1-(iodomethyl)-5-oxo-1,2,4,5-tetrahydrothiazolo[3,2-a]quinazolin-10-ium bromide with potassium iodide and sodium perchlorate yielded the corresponding thiazolo[3,2-a]quinazolinium salts, confirming the stability of the organic cation in ion exchange reactions. Conclusions. This study investigated the regioselectivity of the electrophilic heteroannulation reaction of 3-allyl-2-allylthioquinazolin-4-one under the influence of halo- and chalcogen-containing electrophiles, resulting in monohalide salts of tetrahydrothiazolo[3,2-a]quinazolin-10-ium containing an allyl fragment at the 4-position of the thiazoloquinazoline.
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