利用乙烯酮二硫代缩醛通过水介导构建三取代吡唑/异恶唑文库。

Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals.

作者信息

Savant Mahesh M, Pansuriya Akshay M, Bhuva Chirag V, Kapuriya Naval, Patel Anil S, Audichya Vipul B, Pipaliya Piyush V, Naliapara Yogesh T

机构信息

Department of Chemistry, Chemical Research Laboratory, Saurashtra University, Rajkot, India.

出版信息

J Comb Chem. 2010 Jan-Feb;12(1):176-80. doi: 10.1021/cc900148q.

DOI:10.1021/cc900148q

PMID:19950975

Abstract

A small molecule library of alkyl, sulfone, and carboxamide functionalized pyrazoles and isoxazoles has been developed via a rapid sequential condensation of various alpha-acylketene dithioacetals (1a-o) with hydrazine hydrate or hydroxylamine hydrochloride, followed by oxidation of sulfide to sulfone using water as the reaction medium. An efficient and safe oxidation of sulfides (4/5a-o) to the corresponding sulfones (6/7a-o) using sodium per borate system in aqueous medium is reported. The concise and two step synthesis of trisubstituted pyrazoles and isoxazoles was investigated under variety of reaction condition. The newly developed methodology has the advantage of excellent yield and chemical purity with short reaction time using water as a solvent.

摘要

通过各种α-酰基乙烯酮二硫代乙酸酯（1a - o）与水合肼或盐酸羟胺的快速顺序缩合，随后以水作为反应介质将硫化物氧化为砜，开发了一种由烷基、砜和羧酰胺官能化的吡唑和异恶唑小分子库。报道了在水性介质中使用过硼酸钠体系将硫化物（4/5a - o）高效安全地氧化为相应的砜（6/7a - o）。在各种反应条件下研究了三取代吡唑和异恶唑的简洁两步合成法。新开发的方法具有产率高、化学纯度好、反应时间短且以水为溶剂的优点。