Organic and Biomolecular Chemistry p. 59 - 63 (2015)
Update date:2022-09-26
Topics: NMR spectroscopy Chromatography Solid Support Reaction Vessel Solid phase synthesis Acyl hydrazides
Sarma, Bani Kanta
Liu, Xiaodan
Wu, Hao
Gao, Yu
Kodadek, Thomas
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. This journal is
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