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Issue 33, 2014
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Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

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Abstract

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.

Graphical abstract: Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

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Publication details

The article was received on 06 Feb 2014, accepted on 26 Mar 2014 and first published on 28 Mar 2014


Article type: Paper
DOI: 10.1039/C4RA01053A
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RSC Adv., 2014,4, 17196-17205

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    Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

    M. R. Bodireddy, N. C. G. Reddy and S. D. Kumar, RSC Adv., 2014, 4, 17196
    DOI: 10.1039/C4RA01053A

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