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TBAB-catalyzed cascade reactions: facile synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines via 5-exo-dig cyclization of o-arylalkynylquinoline aldehydes

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Abstract

A convenient method for the facile synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines was developed from the TBAB-catalyzed nucleophilic addition/cyclization reaction of o-arylalkynylquinoline aldehydes with trimethyl trifluoromethyl silane, cesium fluoride, and water; the product was obtained in good to excellent yields. The reaction proceeded smoothly via 5-exo-dig selectivity and anti co-planarity addition, affording Z-selective products in an aerobic atmosphere at room temperature. The dihydrofuroquinoline derivatives formed are structurally related to the well-known furoquinoline alkaloids of the rutaceae family.

Graphical abstract: TBAB-catalyzed cascade reactions: facile synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines via 5-exo-dig cyclization of o-arylalkynylquinoline aldehydes

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Publication details

The article was received on 07 Apr 2017, accepted on 10 Jun 2017 and first published on 03 Jul 2017


Article type: Research Article
DOI: 10.1039/C7QO00273D
Citation: Org. Chem. Front., 2017, Advance Article
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    TBAB-catalyzed cascade reactions: facile synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines via 5-exo-dig cyclization of o-arylalkynylquinoline aldehydes

    K. Mishra, J. B. Singh, T. Gupta and R. M. Singh, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00273D

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