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

被引:0
作者
Hamzeh Kiyani
Hassan Darbandi
Asiyeh Mosallanezhad
Fatemeh Ghorbani
机构
[1] Damghan University,School of Chemistry
来源
Research on Chemical Intermediates | 2015年 / 41卷
关键词
2-Hydroxy-5-sulfobenzoic acid; 1-Amidoalkyl-2-naphthols; Three-component reaction; Water; 3,4-disubstituted isoxazol-5(4; )-ones; Solvent-free;
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摘要
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.
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页码:7561 / 7579
页数:18
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  • [1] Cardellicchio C(2010)Meshram Tetrahedron Asymmetry 21 507-undefined
  • [2] Capozzi MAM(2014)Y. hashimoto Synth. Commun. 44 2468-undefined
  • [3] Naso F(2009)Open Chem. Eur. J. 15 6718-undefined
  • [4] Yang L(1999)undefined Eur. J. Med. Chem. 34 877-undefined
  • [5] Yang Q(2014)undefined J. Med. Chem. Res. 23 939-undefined
  • [6] Shi J(2013)undefined Med. Chem. Res. 22 2005-undefined
  • [7] Wang Y(1972)undefined J. Antibiot. 25 44-undefined
  • [8] Zhang M(1997)undefined Bioorg. Med. Chem. Lett. 7 881-undefined
  • [9] Metlushka KE(1955)undefined J. Am. Chem. Soc. 77 636-undefined
  • [10] Kashemirov BA(2001)undefined Bioorg. Med. Chem. Lett. 11 1851-undefined