The Mannich reaction of 9-acetyl- and 9,10-dihydro-9-acetylanthracene. Reduction of the Mannich bases, and stereochemistry of the 9,10-dihydro compound

S. Foldeak, P. Hegyes, J. Molnar

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Abstract

The Mannich derivatives (2 and 5) of 9-acetyl-9,10-dihydroanthracene (4) with amines of different sizes were prepared for study of their biological effects. It was found that formation of the normal Mannich product in acetic acid was accompanied by formation of a secondary Mannich product containing a methylidene group (3 and 6). Reduction of compounds 5 with NaBH4 gave aminoalcohols (10), and amino-olefins (11) were prepared from these by elimination. The catalytic reduction of compounds 2 on Pd/C, Raney Ni and Adams catalysts was studied under acidic and basic conditions. In acidic media on Pd/C, the 9,10-dihydro compounds (5) were formed; under basic conditions, on all three catalysts the hydrogenation led to deamination. However, for "steric hindrance" reasons the keto group was not reduced in any of the cases. In compounds 5, the literature data and the H-NMR spectra indicate that the orientation of the 9-substituent is pseudoaxial.

Original languageEnglish
Pages (from-to)5913-5918
Number of pages6
JournalTetrahedron
Volume41
Issue number24
DOIs
Publication statusPublished - 1985

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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