Keywords: Nucleophilic vinylic substitution (S N V) mechanism / Enol ethers / Alkoxymethylene compounds / Quinoxalines / Molecular calculationsTreatment of 6-aminoquinoxaline with β,β-diactivated alkoxymethylene derivatives gave the corresponding N-(quinoxalin-6-yl)enamines. A variant of the S N V reaction mechanism was proposed for substitution of the alkoxymethylene compounds, on the basis of the structures of the precursor
The studied 1-(2-benzothiazolyl)-2-pyridones Va-Vf were prepared from N-(2-benzothiazolyl)cyanoacetamide (II) which on reaction with 4-substituted benzaldehydes afforded 3-aryl-N-(2-benzothiazolyl)-2-cyano-2-propenamides IVa-IVg. Compounds IVa-IVf were cyclized with malonodinitrile in the presence of piperidine to give the corresponding pyridones Va-Vf.
Substituted 1-(6-methoxy-2-benzothiazolyl)-2-pyridones 5a-5f have been prepared from N-(6-methoxy-2-benzothiazolyl)cyanoacetamide (2) which on reactions with 4-substituted benzaldehydes gives 3-aryl-2-cyano-N-(6-methoxy-2-benzothiazolyl)-2-propenamides 4a-4g. Derivatives 4a-4f were cyclized with malonodinitrile in the presence of piperidine to give the corresponding 2-pyridones 5a-5f. The IR, UV, 1H NMR and mass spectra of the substances synthesized are discussed.
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