Abstract
A one-pot route was developed for efficient synthesis of novel 2-substituted quinolin-4-carboxamides via a four-component sequential reaction between isatins, ammonium acetate, triethyl orthoacetate, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2H-pyran-2-one. This protocol is an extension of Pfitzinger’s quinoline synthesis and involves an unprecedented in situ iminoacetylation of 2H-pyrone ring at the 3-position followed sequentially by an isatin-ring-opening and a rearranged cyclization reaction. The products are covalently bound couples of quinolin-4-carboxamides and 4-hydroxycoumarin/4-hydroxy-6-methyl-2H-pyran-2-one heterocyclic nuclei with structures that are supported by their NMR, IR, and mass spectral data.
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