导致稠合吡咯的纳扎罗夫环化反应的首个实例。

The first examples of Nazarov cyclizations leading to annulated pyrroles.

作者信息

Song Chuanjun, Knight David W, Whatton Maria A

机构信息

School of Chemistry, Cardiff University, Main College, UK.

出版信息

Org Lett. 2006 Jan 5;8(1):163-6. doi: 10.1021/ol052683z.

DOI:10.1021/ol052683z

PMID:16381593

Abstract

[reaction: see text] Reactions between alpha-substituted unsaturated carboxylic acids 20 and N-tosylpyrroles [14, 23] in the presence of trifluoroacetic anhydride result in smooth alpha-acylation of the pyrrole, followed by Nazarov cyclization to give 50-80% yields of cyclopenta[b]pyrroles. The presence of an alpha-substituent in the unsaturated acid appears to be mandatory.

摘要

[反应：见正文] 在三氟乙酸酐存在下，α-取代的不饱和羧酸20与N-甲苯磺酰基吡咯[14,23]之间的反应可使吡咯顺利进行α-酰化，随后经纳扎罗夫环化反应，得到产率为50 - 80%的环戊并[b]吡咯。不饱和酸中α-取代基的存在似乎是必不可少的。