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Letters in Organic Chemistry

Author(s): S. Karthik, L.V. Priya, B.M. Rao, D.R. Adarsh, B. Sridhar, B.V.S. Reddy* and P. Padmaja*

DOI: 10.2174/0115701786312736240604093915

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Organocatalytic Domino Knoevenagel Hetero-Diels-Alder Reaction for the Synthesis of Chromenopyran Derivatives

Page: [78 - 86] Pages: 9

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Abstract

An organocatalytic, one-pot four-center two-component coupling reaction has been developed for the synthesis of tetrahydro-1H,7H-chromeno[3,4-c]chromen-1-one derivatives. The reaction proceeds smoothly in the presence of 5 mol% DL-Proline in methanol under reflux conditions. This method involves the Knoevenagel condensation of O-alkynyl tethered 2-hydroxybenzaldehydes with cyclic 1,3-diketones followed by an intramolecular hetero-Diels-Alder reaction. Novel classes of oxygen containing polycyclic frameworks are prepared in good yields by using this approach.

Keywords: O-Alkynyl salicylaldehydes, 1, 3-diketones, fused chromenes, hetero-Diels-Alder reaction, organocatalyst, DLProline, propargyl bromide, cyclohexane-1, 3-dione.

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CCDC 2286103 for 5e contains the supplementary crystallographic data for this paper,