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A One‐Pot Copper(II)‐Catalyzed Tandem Synthesis of 2‐Substituted Pyrrolo[1,2‐ b ]pyridazin‐4(1 H )‐ones
Author(s) -
Tan Cun,
Xiang Haoyue,
He Qian,
Yang Chunhao
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500422
Subject(s) - chemistry , pyridazine , tandem , catalysis , copper , quinoline , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
A one‐pot copper(II)‐catalyzed tandem synthesis of 2‐substituted pyrrolo[1,2‐ b ]pyridazin‐4(1 H )‐ones from N ‐aminopyrroles was developed. This tandem reaction involves a Conrad–Limpach‐type reaction, including the thermal condensation of N ‐aminopyrroles with the carbonyl group of β‐oxo esters followed by the cyclization of Schiff base intermediates. Compared to the traditional Conrad–Limpach quinoline synthesis, we herein successfully applied copper(II) as a catalyst in this transformation to furnish 2‐substituted pyrrolo[1,2‐ b ]pyridazin‐4(1 H )‐ones for the first time. Most of the substrates bearing electron‐donating (EDG) and electron‐withdrawing (EWG) groups worked well with this procedure. The corresponding products could be converted directly into diverse pyrrolo[1,2‐ b ]pyridazine for drug discovery and materials science.