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Extra resources for Advances in Heterocycling Chemistry. Vol. 44

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781 (125) For quinoline derivatives substituted with electron-withdrawing groups, such as 3-nitroquinoline (126), the amide ion is not necessary for a-adduct formation. Liquid ammonia is a sufficiently strong nucleophile to attack the highly electron-deficient heterocycle (Scheme 50). The attack occurred at C-4 and was not dependent on temperature in the range of -45 to +20°C. Addition of potassium permanganate gave a 65% yield of 4-amino-3nitroquinoline (127) (85JHC353). It is noteworthy that 4-nitroquinoline in liquid ammonia, with potassium permanganate, gave only 3-amino-4nitroquinoline (86%).

They obtained 'H-NMR spectra of the adducts formed by mixing the diazine in liquid ammonia with sodium or potassium amide. 5 ppm) were typical indicators of adduct formation. In an excess of diazine, both free and complexed diazine were evident in the spectrum, while in an excess of amide, the spectrum did not indicate the presence of free diazine. Pyrazine gave a spectrum consistent with 2-amino-] ,2-dihydropyrazinide (18). Pyrimidine may form adducts in three positions, but the major adduct observed was 4-amino- 1, (or 3), 4-dihydropyrimidinide (19).

5 ppm) were typical indicators of adduct formation. In an excess of diazine, both free and complexed diazine were evident in the spectrum, while in an excess of amide, the spectrum did not indicate the presence of free diazine. Pyrazine gave a spectrum consistent with 2-amino-] ,2-dihydropyrazinide (18). Pyrimidine may form adducts in three positions, but the major adduct observed was 4-amino- 1, (or 3), 4-dihydropyrimidinide (19). Two a-adducts are possible for pyridazine, but the structure found was 4-amino- 1,4dihydropyridazinide (20).

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