Abstract
Background: 1-Amidoalkyl-2-naphthols are an attractive group of organic compounds that can be converted to oxazine heterocycles and aminoalkyl naphthols. The derivatives of 1- amidoalkyl-2-naphthols have significant biological activities and act as drug candidates.
Methods: 1-Amidoalkyl-2-naphthols were synthesized via the three-component condensation reaction of 2-naphthol, acetamide/benzamide and various aldehydes in the presence of 10 mol% of adipic acid as an organocatalyst under solvent-free conditions at 120°C.
Results: A simple, efficient, and operative method for the synthesis of 1-amidoalkyl-2-naphtholes in the presence of adipic acid as the biodegradable catalyst is introduced. Easy operation, acceptable reaction times, eco-friendly, availability of starting materials, simple separation of products, and high yields of products are the significant results of this method.
Conclusion: In this study, 1-amidoalkyl-2-naphthols were synthesized using commercially available reactants in excellent yields and relatively shorter times. In this process, microwave or ultrasonic waves were not used to provide energy for the reaction.
Keywords: 1-amidoalkyl-2-naphthols, adipic acid, aryl aldehyde, green synthesis, solvent-free, three-component reaction.
Graphical Abstract
[1]
Cardellicchio, C.; Annunziata, M.; Capozzi, F.N. The Betti base: the awakening of a sleeping beauty. Tetrahedron Asymmetry, 2010, 21, 507-517.
[http://dx.doi.org/10.1016/j.tetasy.2010.03.020]
[http://dx.doi.org/10.1016/j.tetasy.2010.03.020]
[2]
Singh, R.K.; Bala, R.; Kumar, S. An efficient synthesis of 1-amidoalkyl-2-naphthols catalyzed by zinc oxide nanoparticles under solvent-free conditions. Indian J. Chem., 2016, 55B, 381-386.
[http://dx.doi.org/10.1002/chin.201632102]
[http://dx.doi.org/10.1002/chin.201632102]
[3]
(a)Abou-Elmagd, W.S.I.; Hashem, A.I. Synthesis of 1-amidoalkyl-2-naphthols and oxazine derivatives with study of their antibacterial and antiviral activities. Med. Chem. Res., 2013, 22, 2005-2013.
[http://dx.doi.org/10.1007/s00044-012-0205-9]
(b)Deepam, A.; Viswanadhan, J. Green protocols for the one-pot synthesis of vanillin based aminoalkyl and amidoalkyl naphthols and their antibacterial activity. Orient. J. Chem., 2017, 33, 1354-1365.
[http://dx.doi.org/10.13005/ojc/330336]
(c)Nikalje, A.P.G.; Patel, M.; Ranade, Y.; Deshpande, R.; Rajani, D. Design and synthesis of novel N-substituted morpholino benzamide derivatives as antimicrobial agents. Pharm. Sin, 2012, 3, 462-469. d2018
[http://dx.doi.org/10.1007/s00044-012-0205-9]
(b)Deepam, A.; Viswanadhan, J. Green protocols for the one-pot synthesis of vanillin based aminoalkyl and amidoalkyl naphthols and their antibacterial activity. Orient. J. Chem., 2017, 33, 1354-1365.
[http://dx.doi.org/10.13005/ojc/330336]
(c)Nikalje, A.P.G.; Patel, M.; Ranade, Y.; Deshpande, R.; Rajani, D. Design and synthesis of novel N-substituted morpholino benzamide derivatives as antimicrobial agents. Pharm. Sin, 2012, 3, 462-469. d2018
[4]
Bankar, S.R.; Shelke, S.N. Nanomagnetite-supported molybdenum oxide (nanocat-Fe-Mo): an efficient green catalyst for multicomponent synthesis of amidoalkyl naphthols. Res. Chem. Intermed., 2018, 44, 3507-3521.
[http://dx.doi.org/10.1007/s11164-018-3321-4]
[http://dx.doi.org/10.1007/s11164-018-3321-4]
[5]
Szatmar, I.; Fluop, F. Syntheses and transformations of 1-(α-aminobenzyl)-2-naphthol derivatives. Curr. Org. Synth., 2004, 1, 155-165.
[http://dx.doi.org/10.2174/1570179043485402]
[http://dx.doi.org/10.2174/1570179043485402]
[6]
Soliman, H.A.; Mubarak, A.Y.; El-Mekabaty, A.; Awad, H.M.; Elmorsy, S.S. Eco-friendly synthesis of amidochloroalkylnaphthols and its related oxazepinones with biological evaluation. Monatsh. Chem., 2016, 147, 809-816.
[http://dx.doi.org/10.1007/s00706-015-1536-2]
[http://dx.doi.org/10.1007/s00706-015-1536-2]
[7]
Nagawade, R.R.; Shinde, D.B. Sulphamic acid (H2NSO3H)- catalyzed multicomponent reaction of β-naphthol: an expeditious synthesis of amidoalkyl naphthols. Chin. J. Chem., 2007, 25, 1710-1714.
[http://dx.doi.org/10.1002/cjoc.200790316]
[http://dx.doi.org/10.1002/cjoc.200790316]
[8]
An, L.T.; Lu, X.H.; Ding, F.Q.; Jiang, W.Q.; Zou, J.P. Polymer-supported sulphonic acid catalyzed three‐component one-pot synthesis of α-amidoalkyl-β-naphthols. Chin. J. Chem., 2008, 26, 2117-2119.
[http://dx.doi.org/10.1002/cjoc.200890378]
[http://dx.doi.org/10.1002/cjoc.200890378]
[9]
Hajipour, A.R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A.E. Brønsted acidic ionic liquid as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl 2-naphthols under solvent-free conditions. Tetrahedron Lett., 2009, 50, 5649-5651.
[http://dx.doi.org/10.1016/j.tetlet.2009.07.116]
[http://dx.doi.org/10.1016/j.tetlet.2009.07.116]
[10]
Luo, J.; Zhang, Q. A one-pot multicomponent reaction for synthesis of 1-amidoalkyl-2-naphthols catalyzed by PEG-based dicationic acidic ionic liquids under solvent-free conditions. Monatsh. Chem., 2011, 142, 923-930.
[http://dx.doi.org/10.1007/s00706-011-0522-6]
[http://dx.doi.org/10.1007/s00706-011-0522-6]
[11]
Zolfigol, M.A.; Khazaei, A.; Moosavi-Zare, A.R.; Zare, A.; Khakyzadeh, V. Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts. Appl. Catal. A Gen., 2011, 1, 70-81.
[http://dx.doi.org/10.1016/j.apcata.2011.04.013]
[http://dx.doi.org/10.1016/j.apcata.2011.04.013]
[12]
Borhade, A.V.; Uphade, B.K.; Tope, D.R. Synthesis, characterization, and catalytic application of PbS nanoparticles for the synthesis of amidoalkyl naphthols under solvent-free conditions. Res. Chem. Intermed., 2014, 40, 211-223.
[http://dx.doi.org/10.1007/s11164-012-0956-4]
[http://dx.doi.org/10.1007/s11164-012-0956-4]
[13]
Singh, R.K.; Singh, B.; Duvedi, R.; Kumar, S. Sulfanilic acid: A versatile and efficient catalyst among various organoacids screened for the synthesis of 1-amidoalkyl-2-naphthols under solvent-free condition. Res. Chem. Intermed., 2015, 41, 4083-4099.
[http://dx.doi.org/10.1007/s11164-013-1513-5]
[http://dx.doi.org/10.1007/s11164-013-1513-5]
[14]
Kiasat, A.R.; Mouradzadegun, A.; Saghanezhad, S.J. Poly(4-vinylpyridinium butane sulfonic acid) hydrogen sulfate: An efficient, heterogeneous poly(ionic liquid), solid acid catalyst for the one-pot preparation of 1-amidoalkyl-2-naphthols and substituted quinolines under solvent-free conditions. Chin. J. Catal., 2013, 34, 1861-1868.
[http://dx.doi.org/10.1016/S1872-2067(12)60659-7]
[http://dx.doi.org/10.1016/S1872-2067(12)60659-7]
[15]
ian, H.R.; Yarahmadi, S.; Ghashang, M.; Safari Mehmandosti, M.; N‐Bromosuccinimide catalyzed one-pot and rapid synthesis of acetamidobenzyl naphthols under mild and solvent-free conditions. Chin. J. Chem., 2013, 78, 3361-3366.
[16]
Safari, J.; Zarnegar, Z. Synthesis of amidoalkyl naphthols by nano-Fe3O4 modified carbon nanotubes via a multicomponent strategy in the presence of microwaves. J. Ind. Eng. Chem., 2014, 20, 2292-2297.
[http://dx.doi.org/10.1016/j.jiec.2013.10.004]
[http://dx.doi.org/10.1016/j.jiec.2013.10.004]
[17]
Moghanian, H.; Mobinikhaledi, A.; Blackman, A.G.; Sarough-Farahani, E. Sulfanilic acid-functionalized silica-coated magnetite nanoparticles as an efficient, reusable and magnetically separable catalyst for the solvent-free synthesis of 1-amido- and 1-aminoalkyl-2-naphthols. RSC Adv, 2014, 4, 28176-28185.
[http://dx.doi.org/10.1039/C4RA03676J]
[http://dx.doi.org/10.1039/C4RA03676J]
[18]
Bamoniri, A.; Mirjalili, B.F.; Nazemian, S. Nano silica phosphoric acid: an efficient catalyst for the one-pot synthesis of amidoalkyl naphthols under solvent-free condition. J. Iran. Chem. Soc., 2014, 11, 653-658.
[http://dx.doi.org/10.1007/s13738-013-0336-z]
[http://dx.doi.org/10.1007/s13738-013-0336-z]
[19]
Tayebee, R.; Amini, M.M.; Rostamian, H.; Aliakbari, A. Preparation and characterization of a novel Wells-Dawson heteropolyacid-based magnetic inorganic-organic nanohybrid catalyst H6P2W18O62/pyridino-Fe3O4 for the efficient synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions. Dalton Trans., 2014, 43(4), 1550-1563.
[http://dx.doi.org/10.1039/C3DT51594J] [PMID: 24213526]
[http://dx.doi.org/10.1039/C3DT51594J] [PMID: 24213526]
[20]
Adrom, B.; Hazeri, N.; Maghsoodlou, M.T.; Mollamohammadi, M. Ecofriendly and efficient multicomponent method for preparation of 1-amidoalkyl-2-naphthols using maltose under solvent-free conditions. Res. Chem. Intermed., 2015, 41, 4741-4747.
[http://dx.doi.org/10.1007/s11164-014-1564-2]
[http://dx.doi.org/10.1007/s11164-014-1564-2]
[21]
Ghomi, J.S.; Zahedi, S.; Ghasemzadeh, M.A. AgI nanoparticles as a remarkable catalyst in the synthesis of (amidoalkyl)naphthol and oxazine derivatives: an eco-friendly approach. Monatsh. Chem., 2014, 145, 1191-1199.
[http://dx.doi.org/10.1007/s00706-014-1184-y]
[http://dx.doi.org/10.1007/s00706-014-1184-y]
[22]
Kiyani, H.; Darbandi, H. One-pot three-component synthesis of 1-amidoalkyl-2-naphthols in the presence of phthalimide-N-sulfonic acid. Bulg. Chem. Commun.., 2017, 49, 562-568.
[23]
Kiyani, H.; Darbandi, H.; Mosallanezhad, A.; Ghorbani, F. 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. Res. Chem. Intermed., 2015, 41, 7561-7579.
[http://dx.doi.org/10.1007/s11164-014-1844-x]
[http://dx.doi.org/10.1007/s11164-014-1844-x]
[24]
Hazeri, N.; Maghsoodlod, M.T.; Mostafa, S.; Habibi-Khorassani, J.A.; Safarzaei, M.A. A green protocol for one-pot three-component synthesis of amidoalkyl naphthols catalyzed by succinic acid. Chem. Sci. Trans., 2013, 2, 330-336.
[25]
Chen, W.; Peng, X.W.; Zhong, L.X.; Li, Y.; Sun, R.C. Lignosulfonic acid: a renewable and effective biomass-based catalyst for multicomponent reactions. ACS Sustain. Chem. Eng., 2015, 3, 1366-1373.
[http://dx.doi.org/10.1021/acssuschemeng.5b00091]
[http://dx.doi.org/10.1021/acssuschemeng.5b00091]
[26]
Zare, A.; Ahmadi, S.; Abi, F.; Hekmat-Zadeh, T.; Merajoddin, M.; Hatami, M.; Keshtkar, M.; Khazaei, A. Characterization and application of pyrazinium di(hydrogen sulfate) as a highly efficient catalyst for synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes, 9-aryl-1,8-dioxo-octahydroxanthenes and 1-amidoalkyl/carbamatoalkyl-2-naphthols. Scientia Iranica C, 2015, 22, 2271-2281.
[27]
Khanapure, S.; Jagadale, M.; Salunkhe, R.; Rashinkar, G. Zirconocene dichloride catalyzed multi-component synthesis of 1-amidoalkyl-2-naphthols at ambient temperature. Res. Chem. Intermed., 2016, 42, 2075-2085.
[http://dx.doi.org/10.1007/s11164-015-2136-9]
[http://dx.doi.org/10.1007/s11164-015-2136-9]
[28]
Gong, K.; Wang, H.; Ren, X.; Wang, Y.; Chen, J. β-Cyclodextrin-butane sulfonic acid: an efficient and reusable catalyst for the multicomponent synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions. Green Chem., 2015, 17, 3141-3147.
[http://dx.doi.org/10.1039/C5GC00384A]
[http://dx.doi.org/10.1039/C5GC00384A]
[29]
Madankumar, N.; Pitchumani, K. β-Cyclodextrin-monosulphonic acid catalyzed efficient synthesis of 1-amidoalkyl-2-naphthols. Chem. Select, 2017, 2, 10798-10803.
[http://dx.doi.org/10.1002/slct.201702038]
[http://dx.doi.org/10.1002/slct.201702038]
[30]
Dadhania, H.N.; Raval, D.K.; Dadhania, A.N. Sonochemical synthesis of 2,3-dihydro-4(1H)-quinazolinones and 1-amidoalkyl-2-naphthols using magnetic nanoparticle-supported ionic liquid as a heterogeneous catalyst. Res. Chem. Intermed., 2018, 44, 117-134.
[http://dx.doi.org/10.1007/s11164-017-3093-2]
[http://dx.doi.org/10.1007/s11164-017-3093-2]
[31]
Shaterian, H.R.; Azizi, K.; Fahimi, N. Phosphoric acid supported on alumina: A useful and effective heterogeneous catalyst in the preparation of α-amidoalkyl-β-naphthols, α-carbamato-alkyl-β-naphthols, and 2-arylbenzothiazoles. Arab. J. Chem., 2017, 10, S42-S55.
[http://dx.doi.org/10.1016/j.arabjc.2012.07.006]
[http://dx.doi.org/10.1016/j.arabjc.2012.07.006]
[32]
Zolfigol, M.A.; Baghery, S.; Moosavi-Zare, A.R.; Vahdat, S.M.; Alinezhad, H.; Norouzi, M. Design of 1-methylimidazolium tricyanomethanide as the first nanostructured molten salt and its catalytic application in the condensation reaction of various aromatic aldehydes, amides and β-naphthol compared with tin dioxide nanoparticle. RSC Adv, 2015, 5, 45027-45037.
[http://dx.doi.org/10.1039/C5RA02718G]
[http://dx.doi.org/10.1039/C5RA02718G]
[33]
Mansoor, S.S.; Aswin, K.; Logaiya, K.; Sudhan, S.P.N. ZrOCl2.8H2O: An efficient and recyclable catalyst for the three-component synthesis of amidoalkyl naphthols under solvent-free conditions. J. Saudi Chem. Soc., 2016, 20, 138-150.
[http://dx.doi.org/10.1016/j.jscs.2012.06.003]
[http://dx.doi.org/10.1016/j.jscs.2012.06.003]
[34]
Wang, M.; Song, Z.G.; Liang, Y. Zinc benzenesulfonate-promoted eco-friendly and efficient synthesis of 1-amidoalkyl-2-naphthols. Synth. Commun., 2012, 42, 582-588.
[http://dx.doi.org/10.1080/00397911.2010.527424]
[http://dx.doi.org/10.1080/00397911.2010.527424]
[35]
Narayanan, D.P.; Ramakrishnan, R.M.; Sugunan, S.; Narayanan, B.N. Solvent free one pot synthesis of amidoalkyl naphthols over phosphotungstic acid encapsulated montmorillonite clay catalysts. J. Saudi Chem. Soc., 2017, 21, 538-544.
[http://dx.doi.org/10.1016/j.jscs.2015.10.007]
[http://dx.doi.org/10.1016/j.jscs.2015.10.007]
[36]
Barta, P.; Fülöp, F.; Szatmári, I. Mannich base-connected syntheses mediated by ortho-quinone methides. Beilstein J. Org. Chem., 2018, 14, 560-575.
[http://dx.doi.org/10.3762/bjoc.14.43] [PMID: 29623118]
[http://dx.doi.org/10.3762/bjoc.14.43] [PMID: 29623118]
[37]
Sato, K.; Aoki, M.; Noyori, R.A. “Green” route to adipic acid: Direct oxidation of cyclohexenes with 30 percent hydrogen peroxide. Science, 1998, 281(5383), 1646-1647.
[http://dx.doi.org/10.1126/science.281.5383.1646] [PMID: 9733504]
[http://dx.doi.org/10.1126/science.281.5383.1646] [PMID: 9733504]
[38]
Skoog, E.; Shin, J.H.; Saez-Jimenez, V.; Mapelli, V.; Olsson, L. Biobased adipic acid - The challenge of developing the production host. Biotechnol. Adv., 2018, 36(8), 2248-2263.
[http://dx.doi.org/10.1016/j.biotechadv.2018.10.012] [PMID: 30389426]
[http://dx.doi.org/10.1016/j.biotechadv.2018.10.012] [PMID: 30389426]
[39]
Raj, K.; Partow, S.; Correia, K.; Khusnutdinova, A.N.; Yakunin, A.F.; Mahadevan, R. Biocatalytic production of adipic acid from glucose using engineered Saccharomyces cerevisiae. Metab. Eng. Commun., 2018, 6, 28-32.
[http://dx.doi.org/10.1016/j.meteno.2018.02.001] [PMID: 29487800]
[http://dx.doi.org/10.1016/j.meteno.2018.02.001] [PMID: 29487800]
[40]
Kennedy, G.L., Jr Toxicity of adipic acid. Drug Chem. Toxicol., 2002, 25(2), 191-202.
[http://dx.doi.org/10.1081/DCT-120003259] [PMID: 12024802]
[http://dx.doi.org/10.1081/DCT-120003259] [PMID: 12024802]
[41]
Hartwig, A. Adipic acid. MAK-Collection for Occupational Health and Safety, 2018, 3, 1010-1026. [MAK Value Documentation,
2017].
[http://dx.doi.org/10.1002/3527600418.mb12404kske6218]
[http://dx.doi.org/10.1002/3527600418.mb12404kske6218]
[42]
Jumanath, E.C.; Pradyumnan, P.P. Structural, spectroscopic and thermal property studies of cobalt adipate tetrahydrate single crystals. J. Cryst. Growth, 2017, 479, 83-88.
[http://dx.doi.org/10.1016/j.jcrysgro.2017.09.025]
[http://dx.doi.org/10.1016/j.jcrysgro.2017.09.025]
[43]
Ghorbani-Choghamarani, A.; Rashidimoghadam, S. One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br3 under solvent‐free conditions. Chin. J. Catal., 2014, 35, 1024-1029.
[http://dx.doi.org/10.1016/S1872-2067(14)60029-2]
[http://dx.doi.org/10.1016/S1872-2067(14)60029-2]
[44]
Khabazzadeh, H.; Saidi, K.; Seyedi, N. Cu-exchanged heteropoly acids as efficient and reusable catalysts for preparation of 1-amidoalkyl-2-naphthols. J. Chem. Sci., 2009, 121, 429-433.
[http://dx.doi.org/10.1007/s12039-009-0050-7]
[http://dx.doi.org/10.1007/s12039-009-0050-7]
[45]
Khodaei, M.M.; Khosropour, A.R.; 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, 916-920.
[http://dx.doi.org/10.1055/s-2006-939034]
[http://dx.doi.org/10.1055/s-2006-939034]
[46]
Patil, S.B.; Singh, P.R.; Surpur, M.P.; Samant, S.D. Ultrasound-promoted synthesis of 1-amidoalkyl-2-naphthols via a three-component condensation of 2-naphthol, ureas/amides, and aldehydes, catalyzed by sulfamic acid under ambient conditions. Ultrason. Sonochem., 2007, 14(5), 515-518.
[http://dx.doi.org/10.1016/j.ultsonch.2006.09.006] [PMID: 17145194]
[http://dx.doi.org/10.1016/j.ultsonch.2006.09.006] [PMID: 17145194]
[47]
Zali, A.; Shokrolahi, A. Nano-sulfated zirconia as an efficient, recyclable and environmentally benign catalyst for one-pot three component synthesis of amidoalkyl naphthols. Chin. Chem. Lett., 2012, 23, 269-272.
[http://dx.doi.org/10.1016/j.cclet.2011.12.002]
[http://dx.doi.org/10.1016/j.cclet.2011.12.002]
[48]
Nagawade, R.R.; Shinde, D.B. Synthesis of amidoalkyl naphthols by an iodine-catalyzed multicomponent reaction of β–naphthol. Mendeleev Commun., 2007, 17, 299-300.
[http://dx.doi.org/10.1016/j.mencom.2007.09.018]
[http://dx.doi.org/10.1016/j.mencom.2007.09.018]
[49]
Kiasat, A.R.; Hemat-Alian, L.; Saghanezhad, S.J. Nano Al2O3: an efficient and recyclable nanocatalyst for the one-pot preparation of 1-amidoalkyl-2-naphthols under solvent-free conditions. Res. Chem. Intermed., 2016, 42, 915-922.
[http://dx.doi.org/10.1007/s11164-015-2062-x]
[http://dx.doi.org/10.1007/s11164-015-2062-x]
[50]
Anary-Abbasinejad, M.; Hassanabadi, A.; Kamali-Gharamaleki, M.; Saidipoor, A.; Anaraki-Ardakani, H. Three-component reaction between 2-naphthol, aromatic aldehydes and acetonitrile in the presence of chlorosulfonic acid yields 1-(acetylamino (aryl)methyl)-2-naphthols. J. Chem. Res., 2007, 2007, 644-646.
[http://dx.doi.org/10.3184/030823407X266207]
[http://dx.doi.org/10.3184/030823407X266207]
[51]
Wang, M.; Liang, Y.; Zhang, T.T.; Gao, J.J. Synthesis of 1-amidoalkyl-2-naphthols via three-component condensation of 2-naphthol, aldehydes, and amides/urea. Chem. Nat. Compd., 2012, 48, 185-188.
[http://dx.doi.org/10.1007/s10600-012-0200-x]
[http://dx.doi.org/10.1007/s10600-012-0200-x]
[52]
Singh, R.K.; Duvedi, R. Environment-friendly green chemistry approaches for an efficient synthesis of 1-amidoalkyl-2- naphthols catalyzed by tannic acid. Arab. J. Chem., 2018, 11, 91-98.
[http://dx.doi.org/10.1016/j.arabjc.2014.08.022]
[http://dx.doi.org/10.1016/j.arabjc.2014.08.022]
[53]
Wang, M.; Liang, Y.; Zhang, T.T.; Gao, J.J. Three-component synthesis of amidoalkyl naphthols catalyzed by bismuth(III) nitrate pentahydrate. Chin. Chem. Lett., 2012, 23, 65-68.
[http://dx.doi.org/10.1016/j.cclet.2011.10.008]
[http://dx.doi.org/10.1016/j.cclet.2011.10.008]
[54]
Li, T.; Zhai, X.; Singh, D.; Singh, R.K.; Xu, X. Multicomponent one-pot green synthesis of 1-amidoalkyl-2-naphthols promoted by p-nitrobenzoic acid under solvent-free condition. Asian J. Chem., 2014, 26, 5207-5211.
[http://dx.doi.org/10.14233/ajchem.2014.16707]
[http://dx.doi.org/10.14233/ajchem.2014.16707]
[55]
Selvam, N.P.; Perumal, P.T. A new synthesis of acetamido phenols promoted by Ce(SO4)2. Tetrahedron Lett., 2006, 47, 7481-7483.
[http://dx.doi.org/10.1016/j.tetlet.2006.08.038]
[http://dx.doi.org/10.1016/j.tetlet.2006.08.038]
[56]
Wang, M.; Song, Z.G.; Liang, Y. One-pot synthesis of 1-amidoalkyl-2-naphthols from 2-naphthol, aldehydes, and amides under solvent-free conditions. Org. Prep. Proced. Int., 2011, 43, 484-488.
[http://dx.doi.org/10.1080/00304948.2011.613700]
[http://dx.doi.org/10.1080/00304948.2011.613700]
[57]
Puri, S.; Kaur, B.; Parmar, A.; Kumar, H. One-pot solvent-free sonochemical synthesis of 1-amidoalkyl-2-naphthols. Org. Prep. Proced. Int., 2012, 44, 91-95.
[http://dx.doi.org/10.1080/00304948.2012.643200]
[http://dx.doi.org/10.1080/00304948.2012.643200]
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