title: Solid phase synthesis of 1,3,4-oxadiazin-5 (6R)-one and 1,3,4-oxadiazol-2-one scaffolds from acyl hydrazides.
abstract: Solid phase synthesis of 1,3,4-oxadiazin-5(6R)-one and 1,3,4-oxadiazol-2-one scaffolds from resin-bound acyl hydrazides is described. We demonstrate here that the reactions of resin-bound aryl or hetero-aromatic acyl hydrazides with 2-substituted-2-bromoacetic acids and 4-nitrophenyl chloroformate and subsequent treatment with DIEA lead to intramolecular cyclization reactions to produce six-membered 1,3,4-oxadiazin-5(6R)-ones and five-membered 1,3,4-oxadiazol-2-ones, respectively. We also show that acyl hydrazide-derived 1,3,4-oxadiazol-2-ones may be useful serine hydrolase inhibitors.
authors.affiliation: Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Uttar Pradesh-201314, India.
authors.forename: Bani Kanta
authors.initials: BK
authors.lastname: Sarma
authors.forename: Xiaodan
authors.initials: X
authors.lastname: Liu
authors.forename: Hao
authors.initials: H
authors.lastname: Wu
authors.forename: Yu
authors.initials: Y
authors.lastname: Gao
authors.forename: Thomas
authors.initials: T
authors.lastname: Kodadek
mesh_terms: D000588:Amines / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000588:Amines; D010078:Oxazines; D009584:Nitrogen