V. Saleem Malik

Reusable silica-bonded S-sulfonic acid catalyst for three-component synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes and 2-amino-4H-pyrans in aqueous ethanol

Silica-bonded S-sulfonic acid (SBSSA)-catalyzed, facile, one-pot, three-component coupling of 5,5-dimethyl-1,3-cyclohexanedione (dimedone) or 5,5-dimethyl-1,3-cyclohexanedione, aromatic aldehydes, and malononitrile at reflux temperature is described for preparation of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives. 2-Amino-3-cyano-6-methyl-4-phenyl-4H-pyran-5-ethylcarboxylate derivatives can also be prepared in good yield under the same experimental conditions by use of ethyl acetoacetate, aldehydes, and malononitrile. The catalyst, silica-bonded S-sulfonic acid, was reused and recycled without any loss of activity or product yield.

Kinetics and the mechanism of oxidation of methoxy benzaldehydes by benzimidazolium fluorochromate in an aqueous acetic acid medium

Abstract The oxidation of benzaldehyde (BA) as well as 4-methoxy (4-MBA), 3-methoxy (3-MBA), 2-methoxy (2-MBA), 2,6-dimethoxy (2,6-DMBA), 2,4-dimethoxy (2,4-DMBA), 3,4-dimethoxy (3,4-DMBA), 2,4,6-trimethoxy (2,4,6-TMBA), 3,4,5-trimethoxy (3,4,5-TMBA) and 2,3,4-trimethoxy (2,3,4-TMBA) benzaldehydes by benzimidazolium fluorochromate (BIFC) have been studied in a 50% acetic acid–50% water medium. The oxidation leads to the formation of the corresponding carboxylic acids. The reaction is first order with respect to [BIFC], [S] and [H+]. The reaction was catalysed by H+ ions. The reaction was studied at four different temperatures, and the thermodynamic parameters were calculated. The Exner plot indicated that all of the methoxy-substituted benzaldehydes were oxidized via the same mechanism. Based on the observed kinetics, a suitable mechanism has been proposed.