Koley, Suvajit ; Chowdhury, Sushobhan ; Chanda, Tanmoy ; Janaki Ramulu, B. ; Samai, Subhasis ; Motisa, Lerato ; Singh, Maya Shankar (2015) Lewis acid mediated three-component one-flask regioselective synthesis of densely functionalized 4-amino-1,2-dihydropyridines via cascade Knoevenagel/Michael/cyclization sequence Tetrahedron, 71 (2). pp. 301-307. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2014.11.052
Related URL: http://dx.doi.org/10.1016/j.tet.2014.11.052
Abstract
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 α-oxoketene-N,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.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
ID Code: | 119622 |
Deposited On: | 15 Jun 2021 07:35 |
Last Modified: | 15 Jun 2021 07:35 |
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