CONDENSED ISOQUINOLINES. 13. SYNTHESIS OF 1,2,3,4-TETRAHYDROSPIRO[ISOQUINOLINE-4,1'-CYCLOPENTANE]-3-IMINES AND CONDENSED SPIROCYCLIC SYSTEMS BASED ON THEM
Keywords:
isoquinolineimines, isoquinoquinazoline, condensed isoquinolines, spirocyclic compounds, thienopyrimidoisoquinoline, cyclopentaneAbstract
1-(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].
How to Cite
Kisel, V. M.; Kostyrko, E. O.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2002, 38, 940. [Khim. Geterotsikl. Soedin. 2002, 1079.]
For this article in the English edition, see DOI https://doi.org/10.1023/A:1020969413371
