Chemistry Letters, Vol.38, No.7, 680-681, 2009
Pseudo-intramolecular Cyclization of alpha-Nitro-delta-keto Nitrile Leading to 2-Amino-3-nitro-1,4-dihydropyridines
A novel concept-the pseudo-intramolecular process-is applied to the synthesis of multiply functionalized heterocyclic compounds. Acidic alpha-nitro-delta-keto nitrile easily forms an ammonium salt upon treatment with an amine. When the amine is liberated under equilibrium, an intimate pair, namely, a nucleophilic amine and an electrophilic keto nitrile are located close to each other, is formed; thus the amine efficiently attacks a cyano group of keto nitrile. As a result of subsequent cyclization, 1,4-dihydropyridines containing an amino and a nitro group at the vicinal positions as a partial structure are afforded.