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Sodium Hydroxide Catalyzed N‑Alkylation of (Hetero) Aromatic Primary Amines and N1,C5‑Dialkylation of 4‑Phenyl-2-aminothiazoles with Benzyl Alcohols

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journal contribution
posted on 05.07.2013, 00:00 by Ramachandra Reddy Donthiri, Venkatanarayana Pappula, Darapaneni Chandra Mohan, Hiren H. Gaywala, Subbarayappa Adimurthy
In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.