V. Kisel, E. O. Kostyrko, V. Kovtunenko
Aug 1, 2002
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Journal
Chemistry of Heterocyclic Compounds
Abstract
Abstract1-(2-Bromomethylphenyl)-1-cyclopentanecarbonitrile has been synthesized by the cycloalkylation of (2-methylphenyl)acetonitrile with 1,4-dibromobutane with subsequent bromination of the intermediate product with N-bromosuccinimide. The product serves as a convenient intermediate in the synthesis of derivatives of a series of heterospiro systems. Condensation of it with primary amines leads to the hydrobromides of 1,2,3,4-tetrahydrospiro[isoquinoline-4,1'-cyclopentane]-3-imines, but with vicinal eneamino carbonyl compounds derivatives results in previously undescribed condensed spirocyclic systems, viz. spiro[5H-isoquino[2,3-a]quinazoline-7,1'-cyclopentane] and spiro[4H-thieno[3',2':5,6]pyrimido[1,2-b]isoquinoline-6,1'-cyclopentane].