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A Facile Access to functionalized Indenes and Fused Quinolines by Regioselective 5-enolexo-dig Michael Addition and Cyclization Reaction

Abstract

Herein we reported a facile approach to multi-substituted indenes and cyclopenta[b]quinolines under mild conditions. The reaction proceeds via Michael addition between commercially available cyanoacetate/malonic esters and α,β-unsaturated ketones. The synthetic methodology involves enolate mediated regio- and stereoselective intramolecular 5-enolexo-dig cyclization promoted by a catalytic base. The products formed stereoselectively cis in indenes and trans-isomers for cyclopenta[b]quinolines albeit presence of steric hindrance at a quaternary carbon substituted by active methylene compounds. The reaction pathway was investigated by isolating the reaction intermediate. This synthetic transformation was achieved with various aromatic and heteroaromatic Michael acceptors and desired products were obtained in high to excellent yields. The reaction is scalable up to grams level with only 10 mol% of base.

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Publication details

The article was accepted on 13 Oct 2017 and first published on 13 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02498C
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    A Facile Access to functionalized Indenes and Fused Quinolines by Regioselective 5-enolexo-dig Michael Addition and Cyclization Reaction

    V. Tandon, T. Y. Chaudhari and S. K. Ginotra, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB02498C

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