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化学学报
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化学学报 ›› 1993, Vol. 51 ›› Issue (12): 1203-1208. 上一篇    下一篇

研究论文

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   

  1. 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

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624

本文研究了不同反应条件下3-羟基-5-甲基异恶唑(1)与3-甲基-2- 对氯苯基丁酰氯(2a)的反应,提出了区域选择性合成O-和N-酰化产物的方法.在三乙胺存在下,乙腈为溶剂,1和2a～2e反应得到含量为88～96%的O-酰化产物3a～3e,而若将1 转化为相应的异恶唑硅醚4,再与2a～2i反应,则得到含量为86～97%的N-酰化产物5a～5i.试验表明,在DMAP催化下,3a和5a可发生O-/N-酰基转移反应

关键词: 选择性, 酰基, 酰化, 转移反应, 羟基异恶唑 P, 丁酰氯 P, 硅醚

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

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