Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Russian Journal of Organic Chemistry called Synthesis and Antibacterial Activity of Novel (4-Methoxyphenyl)-tetrahydropyranyl-substituted 1,3,4-Oxadiazoles, Author is Aghekyan, A. A.; Mkryan, G. G.; Panosyan, H. A.; Safaryan, A. S.; Stepanyan, H. M., which mentions a compound: 3326-71-4, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2, Safety of 2-Furoic hydrazide.
Condensation of 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonyl chloride I [R1 = Cl] with hydrazine hydrate, furan-2- and 2,5-dimethylfuran-2-carbohydrazides gave disubstituted hydrazides II [R2 = furan-2-carbonyl, (4,5-dimethylfuran-2-carbonyl), 4-(4-methoxyphenyl)tetrahydropyran-4-carbonyl], whose cyclization formed sym. and unsym. 2,5-disubstituted 1,3,4-oxadiazoles III [R3 = 2-furyl, 4,5-dimethyl-2-furyl, 4-(4-methoxyphenyl)tetrahydropyran-4-yl]. Et 4-[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carboxamido]benzoate IV [R4 = CO2Et] was reacted with hydrazine to obtain N-[4-(hydrazinocarbonyl)-phenyl]-4-(4-methoxphenyl)tetrahydro-2H-pyran-4-carboxamide IV [R4 = C(O)NHNH2]. Treatment of IV [R4 = C(O)NHNH2] latter with tri-Et orthoformate gave a monosubstituted 1,3,4-oxadiazole IV [R4 = 1,3,4-oxadiazol-2-yl], and with carbon disulfide, a 5-sulfanyl-1,3,4-oxadiazole derivative IV [R4 = (5-sulfanyl-1,3,4-oxadiazol-2-yl)] was obtained. The subsequent alkylation of this derivative IV [R4 = (5-sulfanyl-1,3,4-oxadiazol-2-yl)] with 5-metoxyfuran-2-Me and benzylaminocarbonylmethyl chlorides substituted chlorides resulted in the synthesis of the corresponding novel S-substituted oxadiazole derivatives V [R5 = 5-methoxycarbonyl-2-furyl, benzylcarbamoyl]. The synthesized compounds I, II, III, IV and V were tested for their antibacterial activity.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics