Mild and practical method for the α-arylation of nitriles with heteroaryl halides
A mild and transition-metal-free method for theα-arylation of a liphatic nitriles with activated heteroaryl halides was developed using NaHMDS o r KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. The method is applicable to both primary and secondary carbonitriles and a wide range of heteroaryl halides. Selective monoarylation was observed with primary carbonitriles. The operational simplicity and the mild reaction conditions add to the value of this methodas a practical alternative to the preparation of α-heteroaryl carbonitriles.
Klapars, Artis,Waldman, Jacob H.,Campos, Kevin R.,Jensen, Mark S.,McLaughlin, Mark,Chung, John Y. L.,Cvetovich, Raymond J.,Chen, Cheng-Yi
p. 10186 - 10189
(2007/10/03)
A New Synthesis of Aryl Hetaryl Ketones via SRN1 Reaction of Halogenated Heterocycles withPotassiophenylacetonitrile Followed by Phase-Transfer Catalyzed Decyanation
Reaction of halogenated pyridines, quinolines, pyrimidines, and pyrazines with potassiophenylacetonitrile (5) in liquid ammonia under near-uv irradiation affords secondary nitriles, which then undergo oxidative decyanation under phase-transfer catalytic conditions to afford aryl hetaryl ketones in excellent yields.
Hermann, Christine K. F.,Sachdeva, Yesh P.,Wolfe, James F.
p. 1061 - 1065
(2007/10/02)
Synthesis and antiarrhythmic activity of new [(dialkylamino)alkyl]pyridylacetamides
The synthesis of new [(dialkylamino)alkyl]pyridylacetamides is reported. These compounds displayed a potent antiarrhythmic activity, as demonstrated on a model of myocardial infarction in the conscious dog. Structure-activity relationships are discussed within a series of 22 homologues, comparing relative antiarrhythmic properties and cardiac side effects. One of these compounds, 15, has been selected as a candidate for clinical evaluation in man.