Synthesis of 1, 2, 3, 4, 5, 6, 7, 8-Octahydro-1-(4-methoxybenzyl)-2-methylphthalazine Derivative (Studies on the Syntheses of Heterocyclic Compounds. CDXXXI)

Abstract

Grignard reaction of 5, 6, 7, 8-tetrahydro-2-methylphthalazinium iodide (IX) with 4-methoxybenzylmagnesium chloride afforded 1, 2, 5, 6, 7, 8-hexahydro-1-(4-methoxybenzyl)-2-methylphthalazine (X), which was further converted to several kinds of 1-benzylocta-hydrophthalazine derivatives (IV, XI, XII, XIII, XIV, XVII, and XIX). Grewe cyclization of IV to yield 16-azamorphinan (III) resulted in failure.