A novel dual three and five-component reactions between dimedone, aryl aldehydes, and 1-naphthylamine: synthesis and computational studies.

• A parallel three and five-component reactions are introduced between dimedone, aryl aldehydes, and 1-naphthylamine. • An unprecedented five-component route to the synthesis of bis(2-benzyl-5,5-dimethylcyclohexane-1,3-dione)-N- and 4- disubstituted naphthylamine derivatives is explored. • Some novel acridine derivatives are presented. • In-silico approaches such as target prediction, molecular modeling, and estimated values of pharmacokinetic factors of synthesized derivatives are investigated. A series of one-pot, atom-economic, in parallel three and five-component reactions for the synthesis of acridine and bis(2-benzyl-5,5-dimethylcyclohexane-1,3-dione)-N- and 4- disubstituted naphthylamine derivatives under green conditions from the reaction between dimedone, aryl aldehydes, and 1-naphthylamine have been investigated. The three-component route to the synthesis of acridine derivatives is well-known, but the five component route results in bis(2-benzyl-5,5-dimethylcyclohexane-1,3-dione)-N- and 4- disubstituted naphthylamine derivatives, which is an unprecedented pathway and is reported herein for the first time. By this achievement, a broad range of novel acridine and bis(2-benzyl-5,5-dimethylcyclohexane-1,3-dione)-N- and 4- disubstituted naphthylamine derivatives have been synthesized with substantial scores during in silico analyses, including molecular docking, molecular dynamics, and ADMET prediction tools. Acridine derivatives and N ,4-disubstituted naphthylamines appear to interact significantly with 5-HT 2A/C and MAO-A/B, respectively. [Display omitted] [ABSTRACT FROM AUTHOR]