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Additional resources for Advances in Heterocycling Chemistry. Vol. 44
The reaction of 3-trifluoromethylquinoline gave a 3% yield of 4-amino-3-cyanoquinoline and 20% of 3-cyanoquinoline, while from 2-trifluoromethylquinoline, only 2-aminoquinoline was obtained in 69% yield. NH, KMnO, - 330 * 44 CHARLES K. McGlLL AND ANGELA RAPPA & ' / [Sec. B H\ H\ Xylene NaNH, + ~ H,N \ N / ' / The amination of pyrroloquinolines is interesting because of the orientation of the amino groups. Isomeric pyrroloquinolines were successfully aminated in xylene with a threefold molar excess of sodium amide; amination was unsuccessful in liquid ammonia (81JOU1371).
Intramolecular Alkylaminations A variation in the use of alkylamines as aminating agents is the intramolecular nucleophilic cyclization of appropriate 3-aminoalkylpyridines. M c G I L L AND ANGELA RAPPA [Sec. In like manner, 3-(3-pyridyl)propylamine (95) gave 1,2,3,4-tetrahydro-1,8-naphthyridine(96) in 30% yield and 4-(3pyridy1)butylamine (97)afforded 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepine (98) in 87% yield (Scheme 38). The latter compound was also prepared using sodium hydride, potassium hydride, and sodium amide, giving lower yields (73JHC39).
Addition of potassium permanganate at - 40°C afforded 26% 193 and 19% 194,along with 10% 4-amino-1,7-naphthyridine (195),even though the anionic a-adduct of 195 was not observed spectroscopically. Conducting the amination of 182 at room temperature in liquid ammonia with potassium nitrate as oxidant afforded a 56% yield of I94(68JOC1384). The amination of 1,8-naphthyridine (183) with potassium amide in liquid ammonia gave, according to NMR spectroscopy, the C-2 adduct (196)at -40°C and at +lO"C, indicating that this is both the kinetically and thermodynamically controlled product (8 1JOC2134).
Advances in Heterocycling Chemistry. Vol. 44 by Author Unknown