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一锅法铜(I)催化合成3,5-二取代异恶唑。

One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles.

作者信息

Hansen Trond V, Wu Peng, Fokin Valery V

机构信息

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

出版信息

J Org Chem. 2005 Sep 16;70(19):7761-4. doi: 10.1021/jo050163b.

Abstract

[reaction: see text] 3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.

摘要

[反应:见正文] 通过一种简便的一锅三步骤方法,利用原位生成的腈氧化物与末端乙炔之间的区域选择性铜(I)催化环加成反应,可高产率地获得3,5-二取代异恶唑。大多数官能团不干扰该反应,该反应可在水性溶剂中进行且无需隔绝氧气。由于所有试剂均按化学计量使用,副产物的生成被降至最低。

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