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A Metal‐Free Route to 2‐Aminooxazoles by Taking Advantage of the Unique Ring Opening of Benzoxazoles and Oxadiazoles with Secondary Amines
Author(s) -
Joseph Jomy,
Kim Ji Young,
Chang Sukbok
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100910
Subject(s) - ring (chemistry) , amination , chemistry , combinatorial chemistry , pharmacophore , amine gas treating , stereochemistry , organic chemistry , catalysis
Toss an amine into the ring : A new metal‐free protocol for the amination of oxazoles has been developed by using iodobenzene diacetate to couple various oxazoles with amines (see scheme). The reaction proceeds through a ring‐opening and subsequent ring‐closing pathway. The optimal conditions are very mild and the substrate scope is broad, producing a range of 2‐aminooxazoles, an important pharmacophore with high bioactivity.