Synthesis of Cyclohex-3-en(ane)-, 1-Methylcyclohex-3-en(ane)-, and 5-Alkylphenyl-substituted Dodecacarboxylic Acids

Abstract

The synthesis of heterocyclic and mono- and dicarboxamide compounds of various structures and functional substitutions was performed by electrophilic reactions, using chlorides of cyclohexane(ene)-, 1-methylcyclohexane(ene)-, and 5-phenyldodecacarboxylic and their isostructural aliphatic carboxylic acids as acylating reagents and aromatic mono- and difunctionally substituted mono- and aliphatic amines as substrates. N-Cycloacyl derivatives of benzimidazole were obtained for the first time by the acylation of benzimidazole with cyclohex-3-ene(an)-1-methylcyclohex-3-ene(an)carboxylic acid chlorides. The acylation of o-phenylenediamine with corresponding acid chrolides was used to prepare N-alkyl and N-acyl, as well as C-acyl benzimidazole derivatives. Saturated cyclohexane- and 1-methylcyclohexanecarboxylic acids and their chlorides were prepared by the hydrogenation of the corresponding unsaturated cyclohexane-3-ene- and 1-methylcyclohex-3-enecarboxylic acids.