Amidoalkyl Naphthols: Trifluoroacetic Acid (TFA) Catalyzed One-Pot, Multi-Component Synthesis
DOI:
https://doi.org/10.6000/1929-5030.2013.02.04.8Keywords:
Amidoalkyl naphthols, multicomponent reaction, solvent-free conditions, trifluoroacetic acidAbstract
Trifluoroacetic acid (TFA) was found as an efficient catalyst for the synthesis of amidoalkyl naphthols from aromatic aldehydes, β-naphthol and acetamide/benzamide under solvent free condition at 80o C. All the synthesized compounds were characterized by IR, 1H NMR and Mass spectra. The advantages of the new method were good yields, short reaction times, simple work-up, inexpensive and easily available catalyst and economical due to absence of solvent. Therefore, this method could be an attractive alternative to existing methods for the synthesis of biologically important amidoalkyl naphthols.
References
[1] Devi I, Bhuyan PJ. Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo [b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions. Tetrahedron Lett 2004; 45: 8625-27. http://dx.doi.org/10.1016/j.tetlet.2004.09.158
[2] Knapp S. Synthesis of Complex Nucleoside Antibiotics. Chem Rev 1995; 95: 1859-76. http://dx.doi.org/0009-2665/95/0795-1859$15.50/0
[3] Juaristi E. Enantioselective Synthesis of -Amino Acids. New York: John Wiley & Sons 1997.
[4] Shen AY, Tsai CT, Chen CL. Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols. Eur J Med Chem 1999; 34: 877-82. http://dx.doi.org/10.1016/S0223-5234(99)00204-4
[5] Szatmari I, Fulop F. Syntheses and transformations of 1-( - aminobenzyl)-2-naphthol derivatives. Curr Org Synth 2004; 1: 155-65. http://dx.doi.org/10.2174/1570179043485402
[6] Gardner FE, Marth PC, Batjer LP. Spraying with plant growth substances to prevent apple fruit dropping. Science 1939; 90: 208-09. http://dx.doi.org/10.1126/science.90.2331.208
[7] Archer TE, Stokes JD. Residue analysis of - naphthoxyacetic acid and -naphthol on field-sprayed tomatoes by high-pressure liquid chromatography. J Agric Food Chem 1980; 28: 877-80. http://dx.doi.org/10.1021/jf60230a011
[8] Kantevari S, Vuppalapati NVS, Nagarapu L. Montmorillonite K10-catalyzed efficient synthesis of amidoalkyl naphthols under solvent-free conditions. Catal Commun 2007; 8: 1857- 62. http://dx.doi.org/10.1016/j.catcom.2007.02.022
[9] Hossein M, Mohammad B, Majid H. Silica-supported perchloric acid (HClO4-SiO2):-A mild, reusable, and highly efficient heterogeneous catalyst for the synthesis of amidoalkyl naphthols. Chin Chem Lett 2008; 19: 1171-77. http://dx.doi.org/10.1016/j.cclet.2008.06.048
[10] Das B, Laxminarayana K, Ravikanth B, Rao RB. Iodinecatalyzed preparation of amidoalkyl naphthols in solution and under solvent-free conditions. J Mol Catal A Chem 2007; 261: 180-88. http://dx.doi.org/10.1016/j.molcata.2006.07.077
[11] Nagarapu L, Baseeruddin M, Apuri S, Kantevari S. Potassium dodecatungstocobaltate trihydrate (K5CoW12O40 3H2O): A mild and efficient reusable catalyst for the synthesis of amidoalkyl naphthols in solution and under solvent-free conditions. Catal Commun 2007; 8: 1729-34. http://dx.doi.org/10.1016/j.catcom.2007.02.008
[12] Khodaei MM, Khosropour RA, Moghanian H. A simple and efficient procedure for the synthesis of amidoalkyl naphthols by p-TSA in solution or under solvent-free conditions. Synlett 2006; 916-20. http://dx.doi.org/10.1055/s-2006-939034
[13] Patil BS, Singh RP, Surpur PM, Samant SD. Ultrasoundpromoted synthesis of 1-amidoalkyl-2-naphthols via a threecomponent condensation of 2-naphthol, ureas/amides, and aldehydes, catalyzed by sulfamic acid under ambient conditions. Ultrason Sonochem 2007; 14: 515-18. http://dx.doi.org/10.1016/j.ultsonch.2006.09.006
[14] Patil BS, Singh RP, Surpur PM, Samant SD. Cationexchanged resins: Efficient heterogeneous catalysts for facile synthesis of 1-amidoalkyl-2-naphthols from one-pot, threecomponent condensations of amides/ureas, aldehydes and 2-naphthol. Synth Commun 2007; 37: 1659-64. http://dx.doi.org/10.1080/00397910701263858
[15] Shaterian RH, Yarahmadi H, Ghashang M. An efficient, simple, and expeditious synthesis of 1-amidoalkyl-2- naphthols as “drug like” molecules for biological screening. Bioorg Med Chem Lett 2008; 18: 788-92. http://dx.doi.org/10.1016/j.bmcl.2007.11.035
[16] Su WK, Tang WY, Li JJ. Strontium(II) triflate-catalysed condensation of -naphthol, aldehyde, and urea or amides: A facile synthesis of amidoalkyl naphthols. J Chem Res 2008; 3: 123-28. http://dx.doi.org/10.3184/030823408X298508
[17] Shaterian RH, Amirzadeh A, Khorami F, Ghashang M. Environmentally friendly preparation of amidoalkyl naphthols. Synth Commun 2008; 38: 2983-94. http://dx.doi.org/10.1080/00397910802006396
[18] Shaterian RH, Khorami F, Amirzadeh A, Ghashang M. Preparation and application of perchloric acid supported on alumina (Al2O3-HClO4) to the synthesis of -( -amidobenzyl)- -naphthols. Chin J Chem 2009; 27: 815-20. http://dx.doi.org/10.1002/cjoc.200990136
[19] Shaterian RH, Yarahmadi H. Sodium hydrogen sulfate as effective and reusable heterogeneous catalyst for the onepot preparation of amidoalkyl naphthols. Arkivoc 2008; 2: 105-14. http://arkat-usa.org/get-file/23225
[20] Chavan NL, Naik PJ, Nayak SK, Kusurkar RS. Indium(III) chloride: An efficient catalyst for the synthesis of amidoalkyl naphthols. Synth Commun 2010; 40: 2941-47. http://dx.doi.org/10.1080/00397910903340702
[21] Wang M, Song ZG, Liang Y. Zinc benzenesulfonatepromoted eco-friendly and efficient synthesis of 1-amidoalkyl- 2-naphthols. Synth Commun 2012; 42: 582-88. http://dx.doi.org/10.1080/00397911.2010.527424
[22] Shaterian RH, Hosseinian A, Ghashang M. PPA-SiO2- catalyzed multicomponent synthesis of amidoalkyl naphthols. Synth Commun 2008; 38: 3375-89. http://dx.doi.org/10.1080/00397910802138231
[23] Shaterian RH, Yarahmadi H. A modified reaction for the preparation of amidoalkyl naphthols. Tetrahedron Lett 2008; 49: 1297-300. http://dx.doi.org/10.1016/j.tetlet.2007.12.093
[24] Selvam PN, Perumal TP. A new synthesis of acetoamido phenols promoted by Ce(SO4)2. Tetrahedron Lett 2006; 47: 7481-83. http://dx.doi.org/10.1016/j.tetlet.2006.08.038
[25] Ansari SAMK, Sangshetti JN, Kokare ND, Wakte PS, Shinde DB. Oxalic acid-catalyzed solvent-free synthesis of - amidoalkyl--naphthols. Indian J Chem Technol 2010; 17: 71-73. http://dx.doi.org/nopr.nicair.res.in/bitstream/123456789/7278/ 1/IJCT 17(1) 71-73
[26] Nandi GC, Samai S, Kumar R, Singh MS. Atom-efficient and environmentally friendly multicomponent synthesis of amidoalkyl naphthols catalyzed by P2O5. Tetrahedron Lett 2009; 50: 7220-22. http://dx.doi.org/10.1016/j.tetlet.2009.10.055
[27] Hajipour AR, Ghayeb Y, Sheikhan N, Ruoho AE. Bronsted acidic ionic liquid as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl 2-naphthols under solventfree conditions. Tetrahedron Lett 2009; 50: 5649-51. http://dx.doi.org/10.1016/j.tetlet.2009.07.116
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Published
2013-11-25
How to Cite
Kadam, V. S., Khanvilkar, P. R., & Patel, A. L. (2013). Amidoalkyl Naphthols: Trifluoroacetic Acid (TFA) Catalyzed One-Pot, Multi-Component Synthesis. Journal of Applied Solution Chemistry and Modeling, 2(4), 263–268. https://doi.org/10.6000/1929-5030.2013.02.04.8
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