Heterogeneous Amberlyst-15-catalyzed synthesis of complex hybrid heterocycles containing [1,6]-naphthyridine under metal-free green conditions.

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ID: 4036
2019
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Abstract
An efficient green protocol for the synthesis of complex hybrid heterocycles containing [1,6]-naphthyridine and coumarin/pyrazole moieties was established, involving an intramolecular [4 + 2] hetero Diels-Alder reaction as the key step. The biologically significant 12,13-dihydro-6H-benzo[h]chromeno[3,4-b][1,6]naphthyridin-6-ones and 6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b][1,6]naphthyridines were synthesized starting from 2-(N-propargylamino)-arylaldehydes and 3-aminocoumarins or 3-methyl-1-aryl-1H-pyrazol-5-amines in the presence of an Amberlyst-15 catalyst in PEG-200 in good yields. The easy access to diverse complex molecules in a single operation from readily available starting materials, a commercially available, transition metal-free and recyclable catalyst, the use of a green solvent, a very high atom economy and the release of water as the only side product are the highlights of this protocol.
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muthukrishnan2019heterogeneousorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Muthukrishnan, Isravel;Vachan, B S;Karuppasamy, Muthu;Eniyaval, A;Uma Maheswari, C;Nagarajan, Subbiah;Menéndez, J Carlos;Sridharan, Vellaisamy;
Journal Organic & biomolecular chemistry
Year 2019
DOI
10.1039/c9ob01256g
URL
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