15986-81-9Relevant articles and documents
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.
Easy synthesis of pyrazines double substituted at 2 and 3
Nakatani,Yanatori
, p. 1509 - 1510 (2007/10/04)
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