Journal
TETRAHEDRON
Volume 71, Issue 2, Pages 301-307Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.11.052
Keywords
Multicomponent cascade reactions; 4-Amino-1,2-dihydropyridines; Regioselective annulation; Solvent-free conditions; Selective Fe3+ sensing
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Funding
- Science and Engineering Research Board [SB/S1/OC-30/2013]
- Council of Scientific and Industrial Research [02(0072)/12/EMR-II]
- UGC-UKIERI, New Delhi, India [184-16/2013(IC)]
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A highly convergent and regioselective one-pot synthesis of hitherto unreported 4-amino-1,2-dihydropyridines has been achieved via three-component domino coupling (3CDC) of alpha-oxoketeneN,S-arylaminoacetals, aldehydes, and malononitrile in the presence of InCl3 under solvent-free conditions. The merit of this cascade Knoevenagel condensation/Michael addition/cyclization sequence is highlighted by its atom-economy, efficacy of forming consecutive three new bonds (two C-C and one C-N), and one ring in a single operation. Noteworthy, the presence of nitrile and amino groups at 3- and 4-positions of 1,2-dihydropyridine ring makes these compounds excellent precursors for further synthetic renovations. Remarkably, one of the newly synthesized 4-amino-1,2-dihydropyridine exhibited high selectivity and sensitivity for Fe3+ ion over other metal ions. (C) 2014 Elsevier Ltd. All rights reserved.
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