Preparation of 2,2-dimethylchroman-4-ones from 5-alkyl-substituted resorcinols: microwave-assisted synthesis and theoretical calculations

Abstract

The influence of different 5-alkyl-substituted resorcinols on the formation of 2,2-dimethylchroman-4-ones is examined experimentally and theoretically. Structures are fully assigned by means of experimental and theoretical 13C and 1H NMR chemical shifts. Based on experimental and theoretical calculations of Friedel-Crafts acylation, it is possible to explain the formation of 2,2-dimethyl-5-hydroxychroman-4-ones and/or 2,2-dimethyl-7-hydroxychroman-4-ones. Evaluation of their biological activity as cannabinoid receptor ligands is also reported.