Selective reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes

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.

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Selective reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes

Cited by 2 publications

References 8 publications

ChemInform Abstract: Selective Reduction of 6‐Substituted 1,5‐Dinitro‐3‐azabicyclo[3.3.1]non‐6‐enes.

ChemInform Abstract: Selective Reduction of 6‐Substituted 1,5‐Dinitro‐3‐azabicyclo[3.3.1]non‐6‐enes.

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

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