微波辐射下钯催化咪唑并[1,2 - b][1,2,4,5]四嗪的高效C6 -（杂）芳基化反应

Efficient pallado-catalyzed C6-(het)arylation of Imidazo[1,2-b][1,2,4,5]tetrazines under microwave irradiations.

作者信息

Pellegatti Laurent, Vedrenne Emeline, Leger Jean-Michel, Jarry Christian, Routier Sylvain

机构信息

Institut de Chimie Organique et Analytique, Universite d'Orleans, UMR CNRS 6005, rue de Chartres, Orleans Cedex 2, France.

出版信息

J Comb Chem. 2010 Jul 12;12(4):604-8. doi: 10.1021/cc1000456.

DOI:10.1021/cc1000456

PMID:20504029

Abstract

A versatile protocol for the preparation of a library of 5,6-(het)bisarylated imidazo[1,2-b][1,2,4,5]tetrazines is described. Target compounds were obtained in fairly good yields, starting from ethoxy-7-(4-methoxyphenyl)imidazo[1,2-b][1,2,4,5]tetrazine and a large panel of bromoaryl derivatives, using palladium catalysis under microwave irradiation. Compatibility with various chemical groups and heterocycles was proven. Steric and electronic effects do not have any effect on the efficiency of the reaction. Purifications were performed without any difficulties, and the structure of a final compound was proven by crystal X-ray diffraction studies.

摘要

描述了一种通用的方法来制备5,6-（杂）双芳基化咪唑并[1,2-b][1,2,4,5]四嗪文库。以7-（4-甲氧基苯基）咪唑并[1,2-b][1,2,4,5]四嗪乙酯和大量溴芳基衍生物为起始原料，在微波辐射下使用钯催化，以相当高的产率获得了目标化合物。已证明该方法与各种化学基团和杂环具有兼容性。空间和电子效应不会对反应效率产生任何影响。纯化过程没有任何困难，最终化合物的结构通过晶体X射线衍射研究得到证实。