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A Concise Synthesis of Potential COX Inhibitor BRL‐37959 and Analogs Involving Bismuth(III) Catalyzed Friedel−Crafts Acylation
Author(s) -
Ahmed Shamsul Arefin,
Hinz Damon J.,
Jellen Marcus J.,
Hossain M. Mahmun
Publication year - 2018
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201800334
Subject(s) - chemistry , friedel–crafts reaction , benzofuran , acylation , trifluoromethanesulfonate , catalysis , total synthesis , bismuth , combinatorial chemistry , organic chemistry , stereochemistry
We report the development of a concise method of synthesizing possible cyclooxygenase (COX) inhibitor BRL‐37959, which is believed to be a potent nonsteroidal anti‐inflammatory drug (NSAID). The four‐step synthesis greatly increased the efficiency of compound production from commercially available salicylaldehydes. The synthesis involved an optimized, bismuth(III) trifluoromethanesulfonate catalyzed benzoylation of a benzofuran ring.