酰腙的 1,3,4-噁二嗪-5(6R)-酮和 1,3,4-噁二唑-2-酮骨架的固相合成。
Solid phase synthesis of 1,3,4-oxadiazin-5 (6R)-one and 1,3,4-oxadiazol-2-one scaffolds from acyl hydrazides.
机构信息
Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Uttar Pradesh-201314, India.
出版信息
Org Biomol Chem. 2015 Jan 7;13(1):59-63. doi: 10.1039/c4ob01883d.
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.
摘要
本文描述了从树脂结合的酰基酰肼合成 1,3,4-噁二嗪-5(6R)-酮和 1,3,4-噁二唑-2-酮骨架。我们在这里证明，树脂结合的芳基或杂芳基酰基酰肼与 2-取代-2-溴乙酸和 4-硝基苯基氯甲酸酯的反应，以及随后用 DIEA 处理，导致分子内环化反应，分别生成六元 1,3,4-噁二嗪-5(6R)-酮和五元 1,3,4-噁二唑-2-酮。我们还表明，酰基酰肼衍生的 1,3,4-噁二唑-2-酮可能是有用的丝氨酸水解酶抑制剂。
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