顺式-4-羟基-5-炔基吡咯烷酮和顺式-5-羟基-6-炔基哌啶酮的金属催化环异构化反应：呋咱并[3,2-b]吡咯和呋咱并[3,2-b]吡啶的合成

Metal-catalyzed cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones: synthesis of furo[3,2-b]pyrroles and furo[3,2-b]pyridines.

作者信息

Jury Jasmine C, Swamy Nalivela Kumara, Yazici Arife, Morgan Ian R, Willis Anthony C, Pyne Stephen G

机构信息

School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.

出版信息

J Org Chem. 2009 Aug 7;74(15):5523-7. doi: 10.1021/jo9007942.

DOI:10.1021/jo9007942

PMID:19496578

Abstract

Furo[3,2-b]pyrroles and furo[3,2-b]pyridines can be conveniently prepared in good yields from the cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones, respectively, using Ag(I), Pd(II)/Cu(I), or Au(I) catalysis. In one case, the cycloisomerization product was unstable and produced a furan derivative by a ring-opening reaction.

摘要

分别使用Ag(I)、Pd(II)/Cu(I)或Au(I)催化，由顺式-4-羟基-5-炔基吡咯烷酮和顺式-5-羟基-6-炔基哌啶酮的环异构化反应可以方便地高产率制备呋[3,2 - b]吡咯和呋[3,2 - b]吡啶。在一种情况下，环异构化产物不稳定，并通过开环反应生成呋喃衍生物。