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Paper | Regular issue | Vol 43, No. 4, 1996, pp.873-882
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7380
2-Alkyl- and 2-Cyano-substituted 1-Acyl-3,4-epoxy-1,2,3,4-tetrahydroquinolines — Reactions with O-Nucleophiles

Romana Hiessböck and Martin Kratzel*

*Institut für Pharmazeutische Chemie der Universität Wien, Pharmaziezentrum, Althanstrasse 14, A-1090 Wien, Austria


The oxirane ring openint of 1,2,3,4-tetrahydroquinoline 3,4-epoxides with O-nucleophiles is described leading to 3,4-diol derivatives (5 - 7) with well defined stereochemistry. As by-products nitrate esters are formed. The reaction was applied to produce the epimeric epoxide (10) via a four step synthesis.