The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reaction of Grignard reagent with 3,5-dicyanopyridines》. Authors are Lukes, R.; Kuthan, J..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).Application of 1195-58-0. Through the article, more information about this compound (cas:1195-58-0) is conveyed.
Et2O solutions of 3,5-dicyanopyridines reacted at 20-40° with MeMgI (Ia) or EtMgBr (Ib) in 4-6-fold excess to form NH.CR1:C(CN).CR2:C(CN).CHR3 or NH.CR1:C(CN).CHR2.C(CN):CR3. The following were prepared: R1 = R2 = R3 = H (I); R1 = R2 = H, R3 = Me (II); R1 = R3 = H, R2 = Et (III); R1 = Me, R2 = R3 = H (IV); R1 = R3 = Me, R3 = H (V); R1 = R3 = Me, R2 = H (VI); R1 = H, R2 = R3 = Me (VII); R1 = H, R2 = Me, R3 = Et (VIII); R1 = H, R2 = Et, R3 = Me (IX); R1 = R3 = Me, R2 = H (X); R1 = R2 = R3 = Me (XI); R1 = R2 = H, R3 = Me (XII); R1 = R3 = H, R2 = Et (XIII); R1 = R2 = Me, R3 = H (XIV); R1 = R2 = R3 = Me (XV). I with Ia gave 76% XII, I with Ib 65% XIII, II with Ia 66% VII, II with Ib 48% VIII, III with Ia 89% IX, IV with Ia about 43% X and XIV, V with Ia 82% XI, VI with Ia 35% XV.
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