Base-Controlled Divergent Synthesis of 5-Cyanobenzoxepines and Benzofuro[2,3-b]pyridines from 2-Bromophenylacetonitriles and Ynones
In: Organic Letters, Jg. 21 (2019-07-08), S. 5457-5461
Online
unknown
Zugriff:
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.
Titel: |
Base-Controlled Divergent Synthesis of 5-Cyanobenzoxepines and Benzofuro[2,3-b]pyridines from 2-Bromophenylacetonitriles and Ynones
|
---|---|
Autor/in / Beteiligte Person: | Chen, Lu-Lu ; Zhang, Jing-Wen ; Zhu, Jun-Yan ; Yang, Wan-Wan ; Fu, Ji-Ya ; Wang, Yan-Bo ; Chen, Pei ; Zhang, Shuai |
Link: | |
Zeitschrift: | Organic Letters, Jg. 21 (2019-07-08), S. 5457-5461 |
Veröffentlichung: | American Chemical Society (ACS), 2019 |
Medientyp: | unknown |
ISSN: | 1523-7052 (print) ; 1523-7060 (print) |
DOI: | 10.1021/acs.orglett.9b01700 |
Schlagwort: |
|
Sonstiges: |
|