Deconstructing cytisine: The syntheses of (±)-cyfusine and (±)-cyclopropylcyfusine, fused ring analogs of cytisine

Yohannes, Daniel; Procko, Kristen; Lebel, Lorraine A.; Fox, Carol B.; O’Neill, Brian T.

doi:10.1016/j.bmcl.2008.02.078

Cited by 20 publications

(19 citation statements)

References 37 publications

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“…The absolute configuration was studied in Japan [15], and the crystal structure was reported in England, [16]. There is other synthesis of cytisine, [17].…”

Section: Antecedentsmentioning

confidence: 99%

The Chemistry of van de Moer Test for Cytisine

Sánchez‐Viesca

Gómez

2021

EJCS

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Cytisine is an alkaloid with biological activity that is used as medication for smoking cessation treatment. It is a quinolizidine derivative, one ring being 2-pyridinone, and there is a third cycle, a disubstituted piperidine. Thus, the analytical chemistry of this compound is relevant. In this communication we provide the chemistry involved in the spot test for cytisine identification by means of ferric chloride/hydrogen peroxide. The electron flow, step by step, is given from the alkaloid to the final colored products. The sequence is based on the chemical properties of the substrate and reagents, disclosing the series of reactions occurring in this assay. The process is in accordance with the experimental results. We also give the mechanism of cytisine degradation, from a quinolizidine system to 6,8-dimethyl quinoline, which involves an interesting rearrangement.

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“…The absolute configuration was studied in Japan [15], and the crystal structure was reported in England, [16]. There is other synthesis of cytisine, [17].…”

Section: Antecedentsmentioning

confidence: 99%

The Chemistry of van de Moer Test for Cytisine

Sánchez‐Viesca

Gómez

2021

EJCS

View full text Add to dashboard Cite

show abstract

“…This includes the application of the lactam enolate/pyridone addition strategy to provide a new entry to cyfusine, a 'deconstructed' cytisine variant originally reported by Yohannes and co-workers. 5 A full range of halocytisines has been profiled as nicotinic ligands, but only the 3-or 5-monohalo, and 3,5-dihalo variants have been reported, 6 these being prepared from cytisine by halogenation of the pyridone moiety. 4-Substituted cytisines are not accessible from cytisine itself 7 and halogenated variants at this site therefore present a challenge and a gap in terms of structure-activity determination.…”

Section: Figurementioning

confidence: 99%