Category: benzisoxazole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about 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..
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