Synthesis and reactions of methyl 3-(1-adamantyl-carbonyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Abstract

The development of methods for preparing novel adamantane derivatives is a current problem since representatives of this class of compound have a broad spectrum of physiological activity (psychostimulating, immunostimulating, anticancer, analgesic) and are used in medical practice as antiviral, anti-parkinsonian, and other preparations [1][2][3][4]. It is known that adamantyl-substituted pyrazole shows high antibacterial activity and is of interest as a chemotherapeutic agent [2].The 1,3-dipolar cycloaddition of diazo derivatives to unsaturated compounds [5,6] shows promise in the synthesis of five membered nitrogen heterocycles and this opens up broad possibilities for preparing novel, practically important polyfunctional materials of different structure. This methodology was used by us in the case of the synthesis of 3-aminopyrrolidin-2-ones, dihydrooxazolines, and 1,3-propylenediamines of the norbornane series [7][8][9][10].With the aim of preparing compounds containing a nitrogen heterocycle and an adamantane fragment we have, for the first time, in this work studied the 1,3-dipolar cycloaddition of 1-(1-adamantyl)-2-diazoethanone (1) to methyl acrylate. On the basis of the methyl 3-(1-adamantylcarbonyl)-4,5-dihydro-1H-pyrazole-