646522-94-3Relevant academic research and scientific papers
In pursuit of α4β2 nicotinic receptor partial agonists for smoking cessation: Carbon analogs of (-)-cytisine
Coe, Jotham W.,Vetelino, Michael G.,Bashore, Crystal G.,Wirtz, Michael C.,Brooks, Paige R.,Arnold, Eric P.,Lebel, Lorraine A.,Fox, Carol B.,Sands, Steven B.,Davis, Thomas I.,Schulz, David W.,Rollema, Hans,Tingley III, F. David,O'Neill, Brian T.
, p. 2974 - 2979 (2007/10/03)
The preparation and biological activity of analogs of (-)-cytisine, an α4β2 nicotinic receptor partial agonist, are discussed. All-carbon-containing phenyl ring replacements of the pyridone ring system, generated via Heck cyclization protocols, exhibited
Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions: Synthetic and Mechanistic Insights
Coe, Jotham W.,Bianco, Krista E.,Boscoe, Brian P.,Brooks, Paige R.,Cox, Eric D.,Vetelino, Michael G.
, p. 9964 - 9970 (2007/10/03)
Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 °C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.
