55821-72-2

Basic information

• Product Name: cytisine
• Synonyms: cytisine
• CAS NO: 55821-72-2
• Molecular Weight: 190.245
• Mol File: 55821-72-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: cytisine(CAS DataBase Reference)
• NIST Chemistry Reference: cytisine(55821-72-2)
• EPA Substance Registry System: cytisine(55821-72-2)

Safety Data

• Hazardous Substances Data: 55821-72-2(Hazardous Substances Data)

Upstream product

• 101351-46-6 3-cyano-6-oxo-6H-quinolizin-1,7-dicarboxylic acid diethyl ester 
• 100795-79-7 3-aminomethyl-6-oxo-6H-quinolizin-1-carboxylic acid ethyl ester 
• 52600-52-9 ethyl 5-cyano-6-hydroxy-2-methyl-pyridine-3-carboxylate 
• 64119-42-2 ethyl 6-chloro-5-cyano-2-methylnicotinate 
• 103038-00-2 ethyl 5-cyano-2-methylnicotinate 
• 321535-22-2 1'-benzyl-6-methoxy-1',4'-dihydro-[2,3']bipyridinyl-5'-carboxylic acid methyl ester 
• 321535-19-7 6-methoxy-[2,3']bipyridinyl-5'-carboxylic acid methyl ester 
• 321535-35-7 (6-methoxy-[2,3']bipyridinyl-5'-yl)-methanol 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 29681-44-5 5-bromo-3-pyridine carboxylic acid methyl ester 
• 78867-61-5 3-benzyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one 

Downstream Products

• 956928-49-7 (1S,5R)-3-{2-[(2-oxo-3-phenyl-2H-chromen-7-yl)oxy]ethyl}-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one 
• 807310-56-1 (+)-N-benzylcytisine 
• 78867-61-5 (1R,5S)-3-benzyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido-[1,2-a][1,5]diazocin-8-one 
• 485-35-8 cytisine 

Relevant articles and documents

Synthesis of (-)-Cytisine Using a 6- endo aza-Michael Addition

An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.

Total synthesis of (±)-cytisine

(equation presented) The nicotine partial agonist cytisine was prepared in five steps featuring an "in situ" Stille or Suzuki biaryl pyridine coupling. Differentiation of the pyridyl rings was accomplished via selective benzylation and then reduction of a pyridinium ring. The penultimate diazabicyclo[3.3.1]-nonane intermediate was obtained with high diastereoselectivity. A similar sequence has been employed for the synthesis of novel derivative 9-methoxycytisine.