102976-96-5Relevant academic research and scientific papers
Indoloquinolizines and a Convenient Synthesis of Flavoserpentine
Teuber, Hans-Joachim,Quintanilla-Licea, Ramiro,Raabe, Thomas
, p. 1111 - 1120 (2007/10/02)
The reaction of tryptamine hydrochloride with acetoacetaldehyde (as its enol ether or acetal) yields 3-acetyl-7,12-dihydro-2-methyl-6H-indoloquinolizinium chloride (2a), which is investigated with regard to its formation and especially to reduction and oxidation processes.This also applies to the hexahydroquinolizine 4 formed by (stereoselective) disproportionation.The base 7 corresponding to 2a has the character of a pyridone methide, after acetalization or dehydrogenation, however, of a betaine (8, 12).By Clemmensen reduction of 2a or of dehydrogenation product 9a the ethyl derivative flavoserpentine (9e) is formed.With 1,1-dimethoxy-3-pentanone the homologous dihydroquinolizinium salts 19 and 20 are obtained.
