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Synthesis of Pyrazolo[1,2‐ a ]cinnolines via a Rhodium‐Catalyzed Oxidative Coupling Approach
Author(s) -
Xing Li,
Fan Zhoulong,
Hou Chengyu,
Yong Guoping,
Zhang Ao
Publication year - 2014
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.201301009
Subject(s) - chemistry , rhodium , catalysis , aryl , substrate (aquarium) , combinatorial chemistry , oxidative coupling of methane , alcohol , solvent , coupling (piping) , organic chemistry , medicinal chemistry , alkyl , oceanography , geology , mechanical engineering , engineering
An efficient synthetic strategy for the unique class of pyrazolo[1,2‐ a ]cinnolines was developed through a rhodium‐catalyzed oxidative coupling of N ‐aryl‐1 H ‐pyrazol‐5(4 H )‐ones with internal alkynes. This protocol features use of the pyrazolone function in the substrate as an intrinsic directing group, hexafluoroisopropyl alcohol (HFIP) as the solvent, and mild reaction conditions as well as a wide substrate scope.