642016-74-8Relevant academic research and scientific papers
Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: A new MCR strategy
Bodireddy, Mohan Reddy,Reddy, N. C. Gangi,Kumar, Sangita D.
, p. 17196 - 17205 (2014)
A new class of 2-amino-4-(3/2-(alkynyl)/3-(alkenyl)phenyl)-6- phenylnicotinonitriles (6, 7 & 9) has been synthesized with good to excellent isolated yields by the multi-component reaction (MCR) of bromobenzaldehyde (1), malononitrile (2), acetophenone (3), NH4OAc (4) and a series of terminal alkynes (5)/alkenes (8) in the presence of pyrrolidine and Pd-catalyst in a mixture of H2O-DME (1:4 ratio) under reflux conditions in a single step. The Heck-type coupling with terminal olefins takes place stereoselectively with exclusive formation of E-isomers. This new MCR strategy opens new avenues in the development of (i) a diversity-oriented new cyanopyridine based compound library and (ii) new chemical entities other than the present reported molecules.
Divergent syntheses of 2-aminonicotinonitriles and pyrazolines by copper-catalyzed cyclization of oxime ester
Wu, Qifan,Zhang, Yan,Cui, Sunliang
supporting information, p. 1350 - 1353 (2014/04/03)
Copper-catalyzed cyclization of an oxime ester toward divergent heterocycle synthesis is reported. Oxime ester serves as an enamine precursor to cyclize with malononitrile and aldehydes for access to 2-aminonicotinonitriles in a one-pot reaction, while cyclizing with N-sulfonylimines leads to synthesis of pyrazolines.
