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Regioselective and diastereoselective synthesis of two functionalized 1,5-methanoindeno[1,2-d]azocines via a three-component reaction

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Abstract

The morpholine promoted three-component reaction of N-alkylpiperidinone, indane-1,3-dione and 2-arylideneindane-1,3-dione in ethanol at room temperature resulted in the (1H-1,5-methanoindeno[1,2-d]azocin-12-ylidene)-1H-indene-1,3(2H)-dione derivatives in good yields and with exo-configuration. Under similar conditions, the reaction of N-alkylpiperidinone with 2-arylideneindane-1,3-dione afforded 7H-1,5-methanoindeno[1,2-d]azocine-7,12-diones with endo-configuration. The domino reaction is believed to proceed with domino Knoevenagel condensation, Michael addition and aldol condensation reaction.

Graphical abstract: Regioselective and diastereoselective synthesis of two functionalized 1,5-methanoindeno[1,2-d]azocines via a three-component reaction

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Publication details

The article was received on 18 Jan 2018, accepted on 08 May 2018 and first published on 08 May 2018


Article type: Paper
DOI: 10.1039/C8OB00144H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Regioselective and diastereoselective synthesis of two functionalized 1,5-methanoindeno[1,2-d]azocines via a three-component reaction

    J. Cao, J. Sun and C. Yan, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00144H

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