1564-36-9

Upstream product

• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 343-94-2 tryptamine hydochloride 
• 4652-27-1 4-methoxy-3-buten-2-one 

Downstream Products

• 121444-61-9 5,6,9,10,12,17,18,21,22,24-Decahydro-r-9,c-21-dihydroxy-9,21-dimethyl-25-phenyl-t-10,t-22-methanodiindolo<2,3-a;2',3'-a'>cycloocta<1,2-g;5,6-g>dichinolizin-7,19-diylium-dichlorid 
• 121521-77-5 5,6,9,10,12,17,18,21,22,24-Decahydro-r-9,t-21-dihydroxy-9,21-dimethyl-25-phenyl-t-10,t-22-methanodiindolo<2,3-a;2',3'-a'>cycloocta<1,2-g;5,6-g>dichinolizin-7,19-diylium-dichlorid 

Relevant academic research and scientific papers

Indoloquinolizines and a Convenient Synthesis of Flavoserpentine

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.