B. Gangadasu, B. China Raju, V. Jayathirtha Rao
2002
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0
Influential Citations
3
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Journal
Heterocyclic Communications
Abstract
A series of new 2-chloro-5-methylpyridine-3-carbaldehyde imines 3a-o were prepared conveniently by the reaction of 2-chloro-5-methylpyridine carbaldehyde 1 and amines 2a-o in excellent yields. Introduction The imines are an important synthetic organic compounds in that they have been reported as potential herbicides, fungicides, neoplasm inhibitors, antiviral, anti convulsants, anti microbial, anti cancer & tubercular, as plant growth regulators, and also have role in biology (vision and ATP synthesis)." Pyridine Schiff bases are very good synthons for the preparation of α -nornicotin derivatives and as pesticides. The most of the Schiff base reactions are acid catalyzed and are generally carried out by re fluxing the carbonyl compounds and amines lb in a suitable solvent. Imine formation between aliphatic aldehydes & amines requires mild conditions like low temperatures. Some Schiff base preparations were carried out using titanium chloride catalyst, Lewis acids, alumina catalysts and the liberated water removal was achieved by azeotropic means, using KOH/NaOH base and also molecular sieves. fUCT Communication No. 011217 Vol. 8, No. 3, 2002 A simple and convenient preparation of 2-chloro-5 methylpyridine-3-carbaldehyde imines Results and Discussion In continuation of our work on biologically active molecules, and on pesticidal compounds, makes us here to report a simple and convenient preparation of a series of new 2-Chloro-5-methylpyridine-3-carbaldehyde derived imines. 2-Chloro-5-methyl pyridine-3-carbaldehyde was prepared by acetylating the propionaldehyde/benzylamine Schiff base and the resulting enamide was cyclized under Villsmeyer formylation conditions to give the corresponding aldehyde. Thus prepared 2-Chloro-5-methyl pyridine-3-carbaldehyde was used to synthesize a series of new imines (Schiff bases) in excellent yields. The results of these studies are arranged in Table. The general synthetic reaction is depicted in Scheme. The synthesized imines were characterized by spectral means and the spectral data is provided in experimental section.