Oxidation Reaction of Bis-Quinolizidine System: Synthesis of New 2-Methyl-17-Oxosparteine and 2-Methyl-α-Isosparteine

Title: Oxidation Reaction of Bis-Quinolizidine System: Synthesis of New 2-Methyl-17-Oxosparteine and 2-Methyl-α-Isosparteine

Volume: 4 Issue: 1

Author(s): Beata Jasiewicz and Wladyslaw Boczon

Affiliation:

Keywords: Sparteine derivatives, oxidation reaction, IR, MS, 1H and 13C NMR spectroscopy, DFT calculations

Abstract: Susceptibilities of two bis-quinolizidine systems: 2-methylsparteine and 2-phenylsparteine to oxidation reaction using K3Fe(CN)6, KMnO4 and Hg(CH3COO)2 have been determined. Of these two derivatives only 2-methylsparteine has been found to undergo oxidation giving new 2-methyl-17- oxosparteine and 2-methyl-α-isosparteine. The structures of the new compounds have been established by IR, MS and NMR spectroscopies. The experimental evidence has been supported by DFT calculations.

Cite this article as:

Jasiewicz Beata and Boczon Wladyslaw, Oxidation Reaction of Bis-Quinolizidine System: Synthesis of New 2-Methyl-17-Oxosparteine and 2-Methyl-α-Isosparteine, Letters in Organic Chemistry 2007; 4 (1) . https://dx.doi.org/10.2174/157017807780037423