Synthesis of adamantane moiety containing new derivatives by multicomponent passerini reaction.

In 1921, Mario Passerini, a chemist working in Florence, discovered the first multicomponent reaction (IMCR). This reaction was developed by Passerin while studying the properties of isocyanides. This reaction produces α-acyloxyamides by the interaction of isocyanides, aldehydes or ketones with carboxylic acids. Passerini reactions are used in production of drug and total syntheses of biologically relevant natural products. Adamantane and derivatives are used in pharmaceutical products for their various medical properties. Adamantane derivatives are specifically linked to the central nervous system and are used to treat Parkinson’s and Alzheimer’s. This project aims to obtain adamantane containing new derivatives by the Passerini reaction. The Passerini reaction was conducted by the interaction of 1-adamantane carboxylic acid, aldehydes (isobutyl, phenylacetaldehyde, and butyl aldehyde), and ethyl isocyano acetate in dichloromethane at room temperature. The progress of the reaction was monitored by TLC. After finishing, the reaction mixture was concentrated and the residue was purificcated on the column chromatography (SiO2, Hexane/Ethyl acetate, 8/1). The structure of synthesized compounds was established by NMR and IR spectroscopy.