57934-06-2Relevant academic research and scientific papers
Synthesis and Stereochemistry of Some New Diazatricyclic Compounds
Scheiber, Pal,Nemes, Peter
, p. 1033 - 1036 (2007/10/02)
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. - Key Words: 7,11-Diazatricyclo2,7>tridecanes / Cytisine analogues
ADDITION OF GRIGNARD REAGENTS TO 1-ACYL-4-METHOXYPYRIDINIUM SALTS. AN APPROACH TO THE SYNTHESIS OF QUINOLIZIDINONES.
Comins, Daniel L.,Brown, Jack D.
, p. 4549 - 4552 (2007/10/02)
The addition of Grignard reagents to 1-acyl-4-methoxypyridinium salts gives 2-substituted 1-acyl-2,3-dihydropyridones.This reaction was utilized to synthesize (+/-)-epi-myrtine and trans-4-phenylquinolizidin-2-one.
