57023-05-9

Upstream product

• 5693-62-9 2,3,4,5-tetrahydro-6-methoxypyridine 
• 75-52-5 nitromethane 

Downstream Products

• 176042-68-5 1-acetyl-2-(nitromethyl)-1,4,5,6-tetrahydropyridine 
• 144618-89-3 1-acetyl-2-(2-nitromethylene)piperidine 
• 491-40-7 quinolizidin-4-one 
• 50720-19-9 6,7,8,9-tetrahydro-4H-quinolizin-4-one 
• 81978-78-1 1,2,3,6,7,8-hexahydro-4H-quinolizin-4-one 
• 1256093-01-2 (Z)-2-((3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)nitromethylene)piperidine 

Relevant academic research and scientific papers

The synthesis of 3-diazo-2-nitromethylenepiperidine

The synthesis of 3-diazo-2-nitromethylenepiperidine, in six steps from 2-piperidone, is reported. This is the first compound described which contains the 3-diazo-1-nitropropene function. The title compound is stable enough to be isolated and characterised in gram quantities using standard organic chemistry techniques and was used to prepare some 5-aza-spiro[2.5]octane and 4,5,6,7-tetrahydro-1H-pyrazolo-[4,3-b]pyridine derivatives.

Synthetic studies on the ceveratrum alkaloid skeleton

1-(2-Cyclohexenyl-1-carbonyl)-piperidine-2-carboxyaldehyde oxime (23) was prepared in 5 steps from pyridine-2-carboxaldehyde. Oxidation with NaOCl afforded the corresponding nitrile oxide which cyclized to give a 1:1 ratio of diastereomers 2aα,3,4,5,5aα,9,10,11aβ,11cα-decahydro-6H,8H-[1,2]benzisoxazolo[3, 4-ab]quinolizin-6-one (24A) and 2aα,3,4,5,5aα,9,10,11aα,11cα-decahydro-6H,8H-[1,2]benzisoxazolo[3, 4-ab]quinolizin-6-one (24B) in a best yield of 30%.