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Copper‐Catalyzed Synthesis of Substituted 4‐Quinolones using Water as a Benign Reaction Media: Application for the Construction of Oxolinic Acid and BQCA
Author(s) -
Gore Babasaheb Sopan,
Lee Chein Chung,
Lee Jessica,
Wang JehJeng
Publication year - 2019
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.201900286
Subject(s) - chemistry , catalysis , combinatorial chemistry , oxolinic acid , pyridine , copper , formaldehyde , organic chemistry , antibiotics , nalidixic acid , biochemistry , antibiotic resistance
Abstract A copper‐catalyzed three‐component synthetic method has been developed for the synthesis of substituted 4‐quinolone derivatives from substituted 3‐(2‐halophenyl)‐3‐oxopropane, aldehydes and aq. NH 3 using water as an environmentally benign reaction media. Moreover, the synthetic utility of the obtained products has been successfully applied for the synthesis of available oxolinic acid and BQCA drugs. The key features of this approach include commercially available starting materials, broad scope, and moderate to good reaction yields. Reaction with formaldehyde, and other functionalities such as −CN, −NO 2 , −SO 2 Ar, and −COAr were also successful. In addition, reaction with heterocyclic compounds such as 3‐(3‐bromothiophen‐2‐yl)‐3‐oxopropanenitrile proceeded smoothly to afford tetrahydrothieno[3,2‐ b ]pyridine‐6‐carbonitrile analogues. The practicality of the designed protocol was confirmed by gram scale synthesis of two derivatives.