A three-component, one-pot synthesis of 1,8-naphthyridine and isoxazole derivatives and computational elucidation of the mechanism
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An efficient and general method for the synthesis of substituted 3,4-dimethylisoxazolo[5,4-b]pyridine-5-carboxamide and benzo[b][1,8]naphthyridine-3-carboxamide derivatives by using 2,2,6-trimethyl-4H-1,3-dioxin-4-one, benzyl amine, aromatic aldehydes, 2-aminoquinoline, or 5-amino-3-methylisoxazole in the presence of a catalytic amount of p-toluenesulfonic acid or iodine is described. The formation of the products was investigated and the results obtained were also supported by theoretical calculations.
KeywordsIsoxazoles 1,8-Naphthyridines Catalyst Conjugated heterocycles Computational studies
N. Ocal gratefully acknowledges financial support of this work by the Scientific and Technological Research Council of Turkey (TUBITAK, project no. 112T880). I. Erden acknowledges financial support of this work by funds from the National Institutes of Health (grant no. SC1GM082340). The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
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