Tricyclic Pyrazoles: An Efficient Approach to Cannabinoid Analogues with a Tricyclic Framework Incorporating the Pyrrole and Pyrazole Moieties

Abstract

In this paper we report the synthesis of some new cannabinoid analogues that share with rimonabant, a potent and selective CB₁ antagonist, the 2,4-dichlorophenyl and piperidin-1-yl substituents on the pyrazole and amide nitrogens, respectively. The general synthesis involves the preparation of a cyclic ketone condensed with a pyrrole, followed by Claisen condensation with diethyl oxalate; from here, an aza-annulation reaction with a substituted hydrazine followed by an amidation step complete the synthesis.

Key words

cannabinoids - tricyclic pyrazoles - Friedel–Crafts acylation - Claisen condensation - aza-annulation

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