80696-79-3Relevant articles and documents
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.
MYRTINE AND EPIMYRTINE, QUINOLIZIDINE ALKALOIDS FROM VACCINIUM MYRTILLUS
Slosse, P.,Hootele, C.
, p. 4287 - 4294 (2007/10/02)
The structures (including conformation and absolute configuration) of myrtine and epimyrtine, quinolizidine alkaloids from Vaccinium myrtillus, are reported.The two bases are obtainable from pelletierine by Mannich condensation with acetaldehyde, or can be derived stereospecifically by 1,4-nucleophilic addition to enaminones.They have been resolved with tartaric acid.The isomerization of myrtine is discussed.