620-87-1Relevant articles and documents
Synthesis of pyridines and pyrazines using an intramolecular hydroamination-based reaction sequence
Rizk, Toni,Bilodeau, Eric J.-F.,Beauchemin, Andre M.
supporting information; experimental part, p. 8325 - 8327 (2010/01/16)
A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). ρ-Toluenesulfonic acid (2 mol%) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redoxneutral aromatization step to occur.
Vicarious nucleophilic substitution of (chloroalkyl)heterocycles with nitroarenes
Florio, Saverio,Lorusso, Patrizia,Luisi, Renzo,Granito, Catia,Ronzini, Ludovico,Troisi, Luigino
, p. 2118 - 2124 (2007/10/03)
The vicarious nucleophilic substitution of potassium carbanions of the (chloromethyl)pyridines 1a and 1b, (chloromethyl)benzothiazole 1c, (chloromethyl)thiazole 1d, (chloroethyl)thiazole 1e and (chloroethyl) benzothiazole 1f wit nitroarenes, leading to ni
Enamine Rearrangement of 2-Benzylpyridinium Salts to 2-Aminobiphenyls
Fadda, A. A.,Sagitullin, R. S.
, p. 707 - 710 (2007/10/02)
N-Methyl-2-benzylpyridinium iodide (1c) undergoes ring opening and recyclization reactions when heated with methylammonium sulphite to give 2-methylaminobiphenyl (2c), 2-hydroxybiphenyl (3) and 2-benzylpyridine (4).A similar reaction of N-methyl-2-(p-acetylbenzyl)-, N-methyl-2-(p-acetamidobenzyl)-, N-methyl-2-(p-phthalimidobenzyl)-, N-methyl-2-(p-ethylaminobenzyl)-, N-methyl-2-(p-methylethylaminobenzyl)-, and N-methyl-2-butyl-pyridinium iodides (1e, g-k) affords 2-methylamino-4-acetylbiphenyl (2e), 2-methylamino-4-aminobiphenyl (2g = 2h), 2-methylamino-4-ethylaminobiphenyl (2i), 2-methylamino-4-methylethylaminobiphenyl (2j) and N-methyl-2-propylaniline (2k) respectively in good yields.On the other hand, N-methyl-2-(carbamylmethyl)- (1a), N-methyl-2-(cyanomethyl)- (1b) and N-methyl-2-(p-nitrobenzyl)pyridinium iodides (1d) do not undergo such a rearrangement.It has been found that the unquaternized 2-benzylpyridine when heated with methylammonium sulphite undergoes recyclization to 2-methylaminobiphenyl (2k).