Reaction of Aldimine Anions with Vinamidinium Chloride: Three-Component Access to 3-Alkylpyridines and 3-Alkylpyridinium Salts and Access to 2-Alkyl Glutaconaldehyde Derivatives

Abstract

N-tert-Butylimino derivatives of aldehydes were deprotonated with LDA and reacted with vinamidinium chloride to give 2-alkylaminopentadienimine derivatives, which were isolated as their corresponding hydrochloride in 68-81% yield. Reaction of these derivatives with ammonium acetate or salts of primary amines, in n-butanol at 80 degrees C, afforded the corresponding 3-alkylpyridines or 3-alkylpyridinium salts in high yield. Alkaline hydrolysis of 2-alkylaminopentadieneimine derivatives allowed a practical accesss to potassium salts of 2-alkylglutaconaldehyde.