N-Substituted pyridine carboxamide oximes (2) were obtained from the reactions of pyridine hydroxamic acid chloride hydrochlorides (1) with primary amines. The reactions of carboxamide oximes with chloroacetyl chloride in the presence of triethylamine gave the corresponding 3,4-disubstituted-1,2,4-oxadiazin-5-ones (3), which on treatment with P_2S_5 gave in moderate yielded the corresponding 3,4-disubstituted-1,2,4-oxadiazin-5-thiones (4). The reaction of pyridine carboxamide oximes with \alpha-aminoacid ester led to the formation of 3,5-disubstituted-1,2,4-oxadiazin-6-ones (5) in moderate yields. The structures of the prepared compound were evaluated by spectroscopy. Some of the representatives of 3,4-disubstituted-1,2,4- oxadiazin-5-ones, thiones, and 3,5-disubstituted-1,2,4-oxadiazin-6-ones were screened for antibacterial activity using disc diffusion. It was found that all the tested compounds have good antimicrobial activities.
ARIKAN, NEVİN; SÜMENGEN, DOĞAN; and DÜLGER, BAŞARAN (2008) "Synthesis and Antimicrobial Activities of 1,2,4-Oxadiazin-5-one, 6-one and 5-Thiones," Turkish Journal of Chemistry: Vol. 32: No. 2, Article 2. Available at: https://journals.tubitak.gov.tr/chem/vol32/iss2/2