作为羰基合成子的乙腈衍生物。通过连续亲核芳香取代和氧化策略一锅法制备二杂芳基酮。

Acetonitrile derivatives as carbonyl synthons. One-pot preparation of diheteroaryl ketones via a strategy of sequential SNAr substitution and oxidation.

作者信息

Yin Zhiwei, Zhang Zhongxing, Kadow John F, Meanwell Nicholas A, Wang Tao

机构信息

Department of Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA.

出版信息

J Org Chem. 2004 Feb 20;69(4):1364-7. doi: 10.1021/jo030234b.

DOI:10.1021/jo030234b

PMID:14961693

Abstract

The anion of 2-aryl acetonitrile derivatives reacted with a variety of heteroaryl chlorides or bromides in an S(N)Ar manifold to afford intermediate anions which were susceptible to oxidation. The addition of sodium peroxide and aqueous NH(4)OAc solution effected oxidation to afford aryl heteroaryl ketones in good yields. Aryl acetonitrile derivatives are thus umpolung-type synthons of the corresponding aryl carbonyl functionality.

摘要

2-芳基乙腈衍生物的阴离子在亲核芳香取代反应体系中与多种杂芳基氯化物或溴化物反应，生成易被氧化的中间体阴离子。加入过氧化钠和醋酸铵水溶液进行氧化反应，可高产率地得到芳基杂芳基酮。因此，芳基乙腈衍生物是相应芳基羰基官能团的极性翻转型合成子。