“…The success of this protocol suggested that the reaction may be broadened to encompass a wider range of carbonyl derivatives if more prevalent acetonitrile reagents 3 were to participate, affording a synthon for 4 , Figure B . Aryl heteroaryl ketones are of interest both as synthetic intermediates and as structural elements present in several drugs, including the anti-inflammatory agent ketorolac, the estrogen receptor modulator raloxifene, and the anti-arrhythmic agent amiodarone (Figure ). , 1 Alternative carbonyl synthons. 2 Drugs with diaryl ketone subunits. 1 …”
The anion of 2-aryl acetonitrile derivatives reacted with a variety of heteroaryl chlorides or bromides in an S(N)Ar manifold to afford intermediate anions which were susceptible to oxidation. The addition of sodium peroxide and aqueous NH(4)OAc solution effected oxidation to afford aryl heteroaryl ketones in good yields. Aryl acetonitrile derivatives are thus umpolung-type synthons of the corresponding aryl carbonyl functionality.
“…The success of this protocol suggested that the reaction may be broadened to encompass a wider range of carbonyl derivatives if more prevalent acetonitrile reagents 3 were to participate, affording a synthon for 4 , Figure B . Aryl heteroaryl ketones are of interest both as synthetic intermediates and as structural elements present in several drugs, including the anti-inflammatory agent ketorolac, the estrogen receptor modulator raloxifene, and the anti-arrhythmic agent amiodarone (Figure ). , 1 Alternative carbonyl synthons. 2 Drugs with diaryl ketone subunits. 1 …”
The anion of 2-aryl acetonitrile derivatives reacted with a variety of heteroaryl chlorides or bromides in an S(N)Ar manifold to afford intermediate anions which were susceptible to oxidation. The addition of sodium peroxide and aqueous NH(4)OAc solution effected oxidation to afford aryl heteroaryl ketones in good yields. Aryl acetonitrile derivatives are thus umpolung-type synthons of the corresponding aryl carbonyl functionality.
An environmentally and economically sustainable synthesis of 2‐benzoxazyl ketones and 2‐benzothiazyl ketones through FeCl3·6H2O catalyzed tandem reactions of alkynyl bromides with 2‐amino(thio)phenols in [bmim]BF4 has been developed. Remarkable advantages of this new synthetic strategy include high efficiency, readily available starting materials, and recyclable catalyst and reaction medium.
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