Studies on O- and N-acylation of 3-hydroxyisoxazole and their regioselectivity.Ⅱ.regioselective synthesis of O-/N- acylation products of 5-methyl-3-hydroxyisoxazole

Acta Chimica Sinica ›› 1993, Vol. 51 ›› Issue (12): 1203-1208. Previous Articles Next Articles

Original Articles

3-羟基异恶唑的O-和N-酰化及其区域选择性研究 Ⅱ.3-羟基-5-甲基异恶唑O-和N-酰化产物的选择性合成

邵瑞链;职承信

南开大学元素有机化学研究所

发布日期:1993-12-15

Studies on O- and N-acylation of 3-hydroxyisoxazole and their regioselectivity.Ⅱ.regioselective synthesis of O-/N- acylation products of 5-methyl-3-hydroxyisoxazole

SHAO RUILIAN;ZHI CHENGXIN

Published:1993-12-15

Abstract

The acylation of 5-methyl-3-hydroxyisoxazole (I) with 3-methyl-2-(4'-chlorophenyl)butyryl chloride has been studied under different reaction conditions. Synthetic methods, solvents, acid-binding agents and reagent stoichiometry exhibit significant influence on the ratio of O-/N-acylation products of I. O- or N-regioselective acylations of I have been developed. Acylation of I in the presence of triethylamine in acetonitrile yielded mainly O-acylated regioisomers. The trimethylsilyl enol ether of I reacted with acid chlorides in benzene to afford mainly N-acylated regioisomers.

Key words: SELECTIVITY, ACYL GROUP, ACYLATION, TRANSFER REACTIONS

CLC Number:

O621

Cite this article

SHAO RUILIAN;ZHI CHENGXIN. Studies on O- and N-acylation of 3-hydroxyisoxazole and their regioselectivity.Ⅱ.regioselective synthesis of O-/N- acylation products of 5-methyl-3-hydroxyisoxazole[J]. Acta Chimica Sinica, 1993, 51(12): 1203-1208.

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3-羟基异恶唑的O-和N-酰化及其区域选择性研究 Ⅱ.3-羟基-5-甲基异恶唑O-和N-酰化产物的选择性合成

Studies on O- and N-acylation of 3-hydroxyisoxazole and their regioselectivity.Ⅱ.regioselective synthesis of O-/N- acylation products of 5-methyl-3-hydroxyisoxazole

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