一种用于杂芳族化合物催化纳扎罗夫环化反应的通用方法。

A general method for the catalytic nazarov cyclization of heteroaromatic compounds.

作者信息

Malona John A, Colbourne Jessica M, Frontier Alison J

机构信息

Department of Chemistry, University of Rochester, Rochester, New York, 14627, USA.

出版信息

Org Lett. 2006 Nov 23;8(24):5661-4. doi: 10.1021/ol062403v.

DOI:10.1021/ol062403v

PMID:17107097

Abstract

A general, catalytic method for efficient Nazarov cyclization of systems containing heteroaromatic components has been developed. Scandium triflate was identified as the most reactive promoter, and it was found that addition of lithium perchlorate was necessary for synthetically useful catalytic cyclizations. The method was used to synthesize a range of cyclopentanone-fused heteroaromatic systems in 36-97% yield, and the reactivity trends observed demonstrate the impact of polarization on cyclization efficiency. [reaction: see text].

摘要

已开发出一种通用的、催化的方法，用于高效地对含有杂芳族成分的体系进行纳扎罗夫环化反应。三氟甲磺酸钪被确定为反应活性最高的促进剂，并且发现添加高氯酸锂对于具有合成实用性的催化环化反应是必要的。该方法用于以36% - 97%的产率合成一系列环戊酮稠合的杂芳族体系，观察到的反应活性趋势证明了极化对环化效率的影响。[反应：见正文]