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Synthesis and Stereochemistry of Some New Diazatricyclic Compounds
Author(s) -
Scheiber Pál,
Nemes Péter
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419941013
Subject(s) - chemistry , steric effects , acylation , condensation , hydrazine (antidepressant) , ketone , diamine , stereochemistry , molecule , medicinal chemistry , mannich reaction , organic chemistry , catalysis , chromatography , thermodynamics , physics
The diazatricyclic ketone 3 was synthesized by a double Mannich condensation starting from 2‐quinolizidone ( 2 ). Reductions of 3 by complex hydrides and hydrazine gave a mixture of isomeric amino alcohols rac ‐ 4/5 and the diamine 6 , respectively. Compounds rac ‐ 4 and rac ‐ 5 could be separated by selective acylation with 4‐chlorobenzoyl chloride due to the fundamental steric differences in the N → O acyl transfer interactions within the isomeric molecules. The cis ‐ and trans ‐4‐phenyl‐2‐quinolizidones ( rac ‐ 10 , rac ‐ 11 ) also underwent a Mannich condensation affording the same product rac ‐ 12 in both cases.