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Phosphine‐Initiated General‐Base‐Catalyzed Quinolone Synthesis
Author(s) -
Khong San,
Kwon Ohyun
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402039
Subject(s) - chemistry , phosphine , zwitterion , catalysis , phosphonium , base (topology) , carboxylate , alkyne , combinatorial chemistry , quinolone , medicinal chemistry , organic chemistry , molecule , antibiotics , mathematical analysis , biochemistry , mathematics
Phosphinocatalysis provides a new approach toward 3‐substituted‐4‐quinolones. A simple procedure, which uses Ph 3 P as an inexpensive catalyst and S ‐phenyl 2‐( N ‐tosylamido)benzothioates and activated alkynes as starting materials, provides direct access to several 3‐aroyl‐4‐quinolones and methyl 4‐quinolone‐3‐carboxylate esters. The reaction presumably occurs through general base catalysis, with the initial addition of Ph 3 P to the activated alkyne generating the phosphonium enoate zwitterion, which acts as the strong base that initiates the reaction.