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Three‐Component Regioselective Synthesis of Tetrahydrofuro[2,3‐ d ]oxazoles and Their Efficient Conversion to Oxazoles
Author(s) -
Ohura Arisa,
Itoh Toshimasa,
Ishida Hiroaki,
Saito Akio,
Yamamoto Keiko
Publication year - 2017
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.201700074
Subject(s) - regioselectivity , chemistry , oxazole , combinatorial chemistry , component (thermodynamics) , medicinal chemistry , organic chemistry , catalysis , physics , thermodynamics
Iodosylbenzene with triflimide (Tf 2 NH) efficiently promotes a three‐component regioselective synthesis of tetrahydrofuro[2,3‐ d ]oxazoles from homopropargyl alcohols, benzonitrile, and O atoms via oxidative [2+2+1] annulations induced by iodocyclization of the homopropargyl alcohols. In addition, the resulting bicyclic compounds can be converted into 2,4,5‐trisubstituted oxazoles bearing hydroxy groups quantitatively; these oxazole derivatives are cores of PPAR agonist analogues.