The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Dihydropyridines. VII. Reactions of symmetrically alkylated 3,5-dicyanopyridines with sodium borohydride》. Authors are Kuthan, J.; Janeckova, E..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).Electric Literature of C7H3N3. Through the article, more information about this compound (cas:1195-58-0) is conveyed.
cf. ibid. 1495; CA 60, 6817d. NaBH4 reduction of 3,5-dicyanopyridines I-VI gave 3,5-dicyano-1,2- and 1,4-dihydropyridines VII-XVII. I and LiAlH4 gave a mixture of VII and VIII which was separated by chromatography. Two procedures were used in the reduction of I-VI: Method A. EtOH (0.2 ml.) was added to a mixture of 38 mg. NaBH4 and 0.001 mole ground I-VI, and the precipitated product washed with 2.5 ml. cold H2O. Method B. NaBH4 (150 mg.) was added to a mixture of 0.002 mole I-VI and 5 ml. EtOH, the solution diluted with H2O to ∼80 ml. after several hrs., and the precipitated filtered off (starting compound, method, product, % yield, and m.p. given): I, B, VIII, 62, 205-6° (dilute EtOH); I, A, VII, 188-9° (Me2CO-cyclohexane) (VIII was also obtained); II, A, IX, 50, 214-15° (dilute EtOH); III, A, X + XI (92:8), 44, 154-72° (mixture); IV, B, XII, 89, 232-3° (MeOH); V, B, XIV + XV (71:29), 69, 138-69° (mixture); VI, -, XVI + XVII (86:14), 77, 108-22° (mixture). Similar results were obtained by reduction of I-IV with LiAlH4. Oxidation of 1.73 g. 3,5-dicyano-2-methyl-4-ethyl-1,2-dihydropyridine in 70 ml. EtOH with Ag2O from 7 g. AgNO3 gave 91% 3,5-dicyano-2-methyl-4-ethylpyridine (XVIII), m. 68-8.5°, sublimed 55-60°/0.4 mm. Treatment of 1.28 g. XVIII with MeMgI prepared from 750 mg. Mg and 1.9 ml. MeI gave 61% XVII, m. 101-2° (dilute acetone), which was oxidized with MnO2 to VI, m. 70-1°.
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