Premium
Copper Catalysis for Nicotinate Synthesis through β‐ Alkenylation/Cyclization of Saturated Ketones with β ‐Enamino Esters
Author(s) -
Ling Fei,
Xiao Lian,
Fang Lu,
Lv Yaping,
Zhong Weihui
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701031
Subject(s) - chemistry , annulation , enamine , aromatization , intermolecular force , catalysis , condensation , organic chemistry , combinatorial chemistry , medicinal chemistry , molecule , physics , thermodynamics
The first example of a Cu‐catalyzed and 4‐OH‐TEMPO mediated intermolecular [3+3] annulation of saturated ketones with β ‐enamino esters is reported herein, which was successfully used for the synthesis of versatile nicotinates through sequential β‐ C( sp 3 )‐H bond alkenylation, enamine‐carbonyl condensation and aromatization. This protocol tolerates a variety of functional groups, thereby providing a practical and efficient method for the fabrication of 5H ‐chromeno[4,3‐b]pyridin‐5‐one skeletons.