51487-37-7Relevant academic research and scientific papers
Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings
Zhou, Min,Tsien, Jet,Qin, Tian
supporting information, p. 7372 - 7376 (2020/04/09)
Despite the tremendous utilities of metal-mediated cross-couplings in modern organic chemistry, coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking – coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, we report a sulfur (IV) mediated cross-coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion.
The Wolff-Kishner Reduction of 2-Acetonyl Pyrazines and Pyridines. A Novel Rearrangement
Paine III, John B.
, p. 1463 - 1465 (2007/10/02)
Wolff-Kishner reduction of 1-(6-methylpyrazin-2-yl)-2-propanone leads to the formation of 2-isopropyl-6-methylpyrazine (2a), in addition to the expected 6-methyl-2-n-propylpyrazine.The by-product 2a is suggested to arise via a spirocyclopropylidene aza-anion, which serves as a conduit between the initial less-stable secondary 1-(2-pyrazinyl)-2-propyl carbanion and the more stable primary 2-(2-pyrazinyl)-1-propyl carbanion.Similar results were observed for the 1-(3-methylpyrazin-2-yl) and 1-(6-methylpyridin-2-yl)-2-propanones.The extent of by-product formation diminished in the pyridine ring system.Electrophilic activation of the ring appears essential since the benzene ring analog phenylacetone gave no detectable cumene under identical reaction conditions.
