Synthesis and reactions of 3-aryloxiran-2-y1 pyridin-2-y1 methanone. a novel synthesis of triazolopyrimidines and hexaazafluorenones for biological evaluation

ABSTRACT

3-aryloxiran-2-y1 pyridin-2-y1 methanones [Ia,b] were prepared according to our pervious workt [1-3], from arylidenepyridin-2-y1-methanone [4-5]. Compounds Ia,b reacted with different amines such as hydrazine hydrate, p-nitrophenyl hydrazine, hydroxyl amine, and thiourea to give pyrazolylpyridine, isoxazolyl pyridine, and pyridinylpytimidine-2-thione compounds Ia,b, IIIa,b, IVa,d, respectively. Compounds IVa,b were alkylated by methyl iodide to give methyl sulfanyl pyrimidine derivatives V[a,b] which were treated with hydrazine hydrate to give pyrimidinyl hydrazine compounds VIa,b The latter compounds reacted with carbon disulfide, ethyl chloroformate, and aromatic aldehyde in different conditions to produce pyridinyltriazolopyrimidinthione, and pyridinyl pyrimidinyl hydrazone, derivatives VIIa,b, VIIIa,b, and IXa,b, respectively. Compounds VIIa,b were treated with ethyl chloroacetate followed by hydrazine hydrate to give pyridinyl triazolopyrimidinyl acetic acid hydrazide compounds XIa,b which cyclized by using phosphorus pentoxide to give pyridinyl hexaazafluorenone derivatives XIIa,b. Compounds IXa,b reacted with thioglycolic acid to give [pyridinylpyrimidinyl amino]-thiazo1idinone derivatives XIIIa,b