1080-87-1Relevant academic research and scientific papers
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
REACTION OF METHOXY-N-HETEROAROMATICS WITH PHENYLACETONITRILE UNDER BASIC CONDITIONS
Yamanaka, Hiroshi,Ohba, Setsuya
, p. 895 - 909 (2007/10/02)
The monomethoxyl derivatives of various ?-electron deficient N-heteroaromatics reacted with phenylacetonitrile in tetrahydrofuran in the presence of sodium hydride to give α-phenyl-N-heteroareneacetonitriles in the yields ranging from 45 to 78percent.On the contrary, the reaction of these methoxyl derivatives with ethyl cyanoacetate or malononitrile under similar conditions was restricted within narrow limits.The synthesis of benzoyl-N-heteroaromatics by the air-oxidation of α-phenyl-N-hetroareneacetonitriles was described additionally.
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.
2-Pyrazinyl-2-arylalkanenitriles
Katritzky, Alan R.,Yannakopoulou, Konstantina,Thomson, Julie,Saczewski, Franciszek,Pilarski, Boguslaw
, p. 479 - 481 (2007/10/02)
A series of new 2-alkyl-2-(3,4-dialkylphenyl)-2-pyrazineacetonitriles (3) was prepared from readily available starting materials by a simple, efficient, two-step sequence.The products are potential herbicides.
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.
