1080-87-1Relevant articles and documents
Preparation of Heteroaryl Phenylmethanes and a 13C and 15N NMR Spectroscopic Study of their Conjugate Carbanions. Rotational Isomerism and Charge Maps of the Anions and Ranking of the Charge Demands of the Heterocycles
Abbotto, Alessandro,Alanzo, Vito,Bradamante, Silvia,Pagani, Giorgio A.
, p. 481 - 488 (2007/10/02)
2-Benzylpyridazine, 4-benzylpyrimidine, 2-benzylpyrimidine and 2-benzylpyrazine, (5-8) have been prepared in order to study their 13C and 15N spectra and those of their conjugate carbanions (1-4).These systems are aza-homologues of the previously reported
A New Synthesis of Aryl Hetaryl Ketones via SRN1 Reaction of Halogenated Heterocycles withPotassiophenylacetonitrile Followed by Phase-Transfer Catalyzed Decyanation
Hermann, Christine K. F.,Sachdeva, Yesh P.,Wolfe, James F.
, p. 1061 - 1065 (2007/10/02)
Reaction of halogenated pyridines, quinolines, pyrimidines, and pyrazines with potassiophenylacetonitrile (5) in liquid ammonia under near-uv irradiation affords secondary nitriles, which then undergo oxidative decyanation under phase-transfer catalytic conditions to afford aryl hetaryl ketones in excellent yields.
SRN1 Mechanism in Heteroaromatic Nucleophilic Substitution. Reactions Involving Halogenated Pyrimidines, Pyridazines, and Pyrazines
Carver, David R.,Komin, Andrew P.,Hubbard, James S.,Wolfe, James S.
, p. 294 - 299 (2007/10/02)
Reactions of 2-chloropyrimidine (1), 4-chloro-2,6-dimethoxypyrimidine (7), 3-chloro-6-methoxypyridazine (9), and 2-chloropyrazine (14) with a representative series of ketone enolates in liquid ammonia exhibited characteristics consistent with a radical-chain (SRN1) mechanism for substituton.Diazines 1 and 9 showed an unexpected sensitivity to enolate ion structure, with 1 reacting best with tertiary enolates and 9 undergoing substitution most satisfactorily with primary enolates.The order of SRN1 reactivity among the various substrates was found to be 14 > 9 > 7 =ca. 1.Thus 1 and 7 required photostimulation at 35o nm for satisfactory displacemement of chloride, 9 underwent some substitution without illumination, and 14 reacted smoothly in the dark.