Benzomorphan related compounds. XIV. Synthesis of 2??(2??pyrrolylmethyl)??and 2??(2??indolylmethyl) tetrahydropyridines and cyclization to pyrrolo [3, 2??f] morphans

J Bosch, D Mauleón, F Boncompte…

Index: Bosch; Mauleon; Boncompte; Granados Journal of Heterocyclic Chemistry, 1981 , vol. 18, # 2 p. 263 - 270

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Citation Number: 16

Abstract

Abstract The synthesis of 2-{2-pyrrolylmethyl)-and 2-(2-indolylmethyl) tetrahydropyridines by condensation of 2-cyanopyridines with appropriate pyrrole or indole derivatives followed by ketone reduction, quaternization and sodium borohydride reduction are described. The acid- induced cyclization of 2-(2-pyrrolylmethyl) tetrahydropyridines affords 4, 5, 6, 7, 8, 9- hexahydro-4, 8-methanopyrrolo [2, 3-d] azocine systems (pyrrolo [3, 2-f]-morphans), ...