Preparation of 3,5-Disubstituted Pyrazoles and Isoxazoles from Terminal Alkynes, Aldehydes, Hydrazines, and Hydroxylamine

被引：129

作者：

Harigae, Ryo ^{[1
]}

Moriyama, Katsuhiko ^{[1
]}

Togo, Hideo ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Inage Ku, Chiba 2638522, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 05期

关键词：

ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; FULLY SUBSTITUTED PYRAZOLES; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; 3-COMPONENT SYNTHESIS; FACILE PREPARATION; MOLECULAR-IODINE; RING-SYSTEMS; DIACETYLENIC KETONES;

D O I：

10.1021/jo4027116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of terminal alkynes with n-BuLi, and then with aldehydes, followed by the treatment with molecular iodine, and subsequently hydrazines or hydroxylamine provided the corresponding 3,5-disubstituted pyrazoles or isoxazoles in good yields with high regioselectivity, through the formations of propargyl secondary alkoxides and alpha-alkynyl ketones. The present reactions are one-pot preparation of 3,5-disubstituted pyrazoles from terminal alkynes, aldehydes, molecular iodine, and hydrazines, and 3,5-disubstituted isoxazoles from terminal alkynes, aldehydes, molecular iodine, and hydroxylamine.

引用

页码：2049 / 2058

页数：10

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