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Issue 100, 2015
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Expedient, catalyst-free, three-component synthesis of fused tetrahydropyridines in water

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Abstract

A catalyst-free, three-component reaction between amino alcohols, 1,3-dicarbonyl compounds and α,β-unsaturated aldehydes was developed for the synthesis of fused tetrahydropyridines in water. The β-enaminone formation-initiated domino sequence afforded oxazolo[3,2-a]pyridines and pyrido[2,1-b][1,3]oxazines diastereoselectivity in good yields involving Michael addition, intramolecular cyclization and iminium ion cyclization steps. This environmentally benign protocol is highly atom-economical where the only side product was two molecules of water and no catalyst or reagent was employed. Besides, in a single operation, four new bonds including two C–N, one C–O and one C–C bonds and two heterocyclic rings were created. The reaction was also effective in various green solvents such as glycerol, PEG-200 and lactic acid.

Graphical abstract: Expedient, catalyst-free, three-component synthesis of fused tetrahydropyridines in water

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Publication details

The article was received on 13 Jul 2015, accepted on 17 Sep 2015 and first published on 22 Sep 2015


Article type: Paper
DOI: 10.1039/C5RA18804K
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2015,5, 81881-81888
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    Expedient, catalyst-free, three-component synthesis of fused tetrahydropyridines in water

    P. Vinoth, P. S. R. Prasad, T. Vivekanand, C. U. Maheswari, S. Nagarajan, J. C. Menéndez and V. Sridharan, RSC Adv., 2015, 5, 81881
    DOI: 10.1039/C5RA18804K

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