2-Hydroxy-5-sulfobenzoic acid: an efficient organocatalyst for the three-component synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones

2-Hydroxy-5-sulfobenzoic acid: an efficient organocatalyst for the three-component synthesis of... 2-Hydroxy-5-sulfobenzoic acid (2-HSBA) efficiently catalyzed the one-pot three-component synthesis of a wide variety of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones. The three-component process of substituted benzaldehydes, 2-naphthol, and amides (benzamide and acetamide) or urea occur using 10 mol% of 2-HSBA as an organocatalyst under solvent-free reaction conditions (SFRCs) at 100 °C. It was also found that the best results for the preparation of 3,4-disubstituted isoxazol-5(4H)-ones were achieved using 15 mol% of 2-HSBA under aqueous conditions at room temperature. The reactions are easy to do and were completed within 3–25 min (for amidoalkyl naphthols), and 70–120 min (for 3,4-disubstituted isoxazol-5(4H)-ones), while the expected products were obtained in 82–97 % yields. The catalyst can be recovered and reused several times in the template reactions. This procedure offers the advantages of convenience, simple operational procedure, cost-effectiveness, no use of hazardous organic solvents, and the commercial availability of the catalyst. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

2-Hydroxy-5-sulfobenzoic acid: an efficient organocatalyst for the three-component synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones

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Publisher
Springer Netherlands
Copyright
Copyright © 2014 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-014-1844-x
Publisher site
See Article on Publisher Site

Abstract

2-Hydroxy-5-sulfobenzoic acid (2-HSBA) efficiently catalyzed the one-pot three-component synthesis of a wide variety of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones. The three-component process of substituted benzaldehydes, 2-naphthol, and amides (benzamide and acetamide) or urea occur using 10 mol% of 2-HSBA as an organocatalyst under solvent-free reaction conditions (SFRCs) at 100 °C. It was also found that the best results for the preparation of 3,4-disubstituted isoxazol-5(4H)-ones were achieved using 15 mol% of 2-HSBA under aqueous conditions at room temperature. The reactions are easy to do and were completed within 3–25 min (for amidoalkyl naphthols), and 70–120 min (for 3,4-disubstituted isoxazol-5(4H)-ones), while the expected products were obtained in 82–97 % yields. The catalyst can be recovered and reused several times in the template reactions. This procedure offers the advantages of convenience, simple operational procedure, cost-effectiveness, no use of hazardous organic solvents, and the commercial availability of the catalyst.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 18, 2014

References

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