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-
Keywords: 3-aminopyrrolidin-2-ones, methyl esters of 1H-pyrazoline-3-carboxylic acids, Raney nickel, catalytic hydrogenation, cyclocondensation.At the present time much attention is paid to the search for new regioselective and stereoselective methods for constructing the pyrrolidine ring, which is a pharmacophoric group of many pharmaceutical preparations (piracetam, oxiracetam, fenotropil) and physiologically active substances (domoic acid, oxazolomycin) [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Pyrrolidines with an amino group in position 3 are of special interest. For example, 3-aminopyrrolidin-2-one, linked with a norbornane fragment, displays antiarrhythmic, anti-inflammatory, analgesic, and nootropic activity and in the breadth of its therapeutic action exceeds the antiarrhythmic preparations used at the present time [15,16].The use of 1,3-dipolar cycloaddition of diazo compounds to olefins and subsequent catalytic hydrogenation of the resulting pyrazolinecarboxylic acid esters is one of the most promising approaches to the synthesis of 3-aminopyrrolidin-2-ones [15][16][17][18].With the aim of obtaining new compounds of the series mentioned the hydrogenation has been studied in the present work of pyrazoline-3-carboxylic acid methyl ester (1), and also its 4-phenyl-(2), 5-methoxycarbonyl-(3), 4-methoxycarbonyl-(4), and 4,5-di(methoxycarbonyl)-(5) substituted analogs.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.