Lu-lu Chen, Jing-Wen Zhang, Pei Chen
Jul 8, 2019
Citations
0
Influential Citations
21
Citations
Journal
Organic letters
Abstract
An effective base-controlled divergent annulation reaction of 2-bromophenylacetonitriles and ynones has been developed. Various functionalized 5-cyanobenzoxepines and benzofuro[2,3- b]pyridines were obtained with a broad substrate scope and high regioselectivity in moderate to excellent yield. Of importance, an unexpected O-rearrangement reaction to access benzofuro[2,3- b]pyridines was observed using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base, and the possible mechanism was supported by 18O-labeled experiments. In addition, the gram-scale synthesis and further transformation of the product were studied.