v-Triazolines. Part 36. New synthesis of ethyl 1-alkyl-1, 4, 5, 6-tetrahydro-6-oxopyridine-3-carboxylates and 1-alkyl-1, 4, 5, 6-tetranydro-6-oxopyridine-3-carbonitriles …

R Angelini, E Erba, D Pocar

Index: Angelini, Roberto; Erba, Emanuela; Pocar, Donato Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 8 p. 837 - 840

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Abstract

Ethyl 1-alkyl-1, 4-dihydropyridine-3-carboxylates 2a–d and 1-alkyl-1, 4-dihydropyridine-3- carbonitriles 2e, f were allowed to react with 2-nitrophenyl azide 3 to give tertiary amidines 4 by spontaneous rearrangement of the triazoline cycloadducts. Ready catalytic hydrogenation with Pd–C of 4 gave the corresponding ethyl 1-alkyl-6-oxo-1, 4, 5, 6- tetrahydropyridine-3-carboxylates 5a–d and 1-alkyl-6-oxo-1, 4, 5, 6-tetrahydropyridine-3- ...