173848-70-9Relevant academic research and scientific papers
Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation
Hardegger, Leo A.,Habegger, Jacqueline,Donohoe, Timothy J.
supporting information, p. 3222 - 3225 (2015/07/15)
A novel methodology for the synthesis of highly substituted pyridines based on the palladium-catalyzed enolate α-alkenylation of ketones is presented; the formation of aromatic compounds is a new direction for this catalytic C-C bond forming reaction. In the key step, a protected β-haloalkenylaldehyde participates in α-alkenylation with a ketone to afford a 1,5-dicarbonyl surrogate, which then undergoes cyclization/double elimination to the corresponding pyridine product, all in one pot. The β-haloalkenylaldehyde starting materials can be obtained from the corresponding methylene ketone via Vilsmeier haloformylation. Using this concise route, a variety of highly substituted pyridines were synthesized in three steps from commercially available compounds. (Chemical Equation Presented).
Gallium (iii)-catalysed bromocyanation of alkynes: Regio- and stereoselective synthesis of β-bromo-α,β-unsaturated nitriles
Murai, Masahito,Hatano, Ryo,Kitabata, Sachie,Ohe, Kouichi
supporting information; experimental part, p. 2375 - 2377 (2011/04/18)
Treatment of arylacetylenes and cyanogen bromide in ClCH2CH 2Cl with a catalytic amount of GaCl3 afforded (Z)-β-bromoacrylonitriles with high regio- and stereoselectivity.
Effect of substituents on the competition between several mechanisms of nucleophilic vinylic substitution
Amatore, Christian,Galli, Carlo,Gentili, Patrizia,Guarnieri, Alessandra,Schottland, Ettie,Rappoport, Zvi
, p. 2341 - 2350 (2007/10/03)
In an attempt to encourage vinylic substrates to undertake an SRN1-like nucleophilic substitution route, a process that requires acquisition of one electron, a series of stilbene halides bearing one electron-withdrawing substituent on the doubl
