P₂O₅ supported on SiO₂ as an efficient and reusable catalyst for rapid one-pot synthesis of carbamatoalkyl naphthols under solvent-free conditions

References

• Bettanin, L., Botteselle, G. V., Godoi, M., & Braga, A. L. (2014). Green synthesis of 1,3-diynes from terminal acetylenes under solvent-free conditions. Green Chemistry Letters and Reviews, 7, 105–112. doi:10.1080/17518253.2014.895868
   Google Scholar
• Brauch, S., van Berkel, S. S., & Westermann, B. (2013). Higher-order multicomponent reactions: Beyond four reactants. Chemical Society Reviews, 42, 4948–4962. doi:10.1039/c3cs35505e
   Google Scholar
• Davoodnia, A., Allameh, S., Fazli, S., & Tavakoli-Hoseini, N. (2011). One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst. Chemical Papers, 65, 714–720. doi:10.2478/s11696-011-0064-8
   Google Scholar
• Davoodnia, A., Basafa, S., & Tavakoli-Hoseini, N. (2016). Neat synthesis of octahydroxanthene-1,8-diones, catalyzed by silicotungstic acid as an efficient reusable inorganic catalyst. Russian Journal of General Chemistry, 86, 1132–1136. doi:10.1134/S107036321605025X
   Google Scholar
• Davoodnia, A., Khashi, M., & Tavakoli-Hoseini, N. (2013). Tetrabutylammonium hexatungstate [TBA]2[W6O19]: Novel and reusable heterogeneous catalyst for rapid solvent-free synthesis of polyhydroquinolines via unsymmetrical Hantzsch reaction. Chinese Journal of Catalysis, 34, 1173–1178. doi:10.1016/S1872-2067(12)60547-6
   Google Scholar
• Davoodnia, A., Tavakoli-Nishaburi, A., & Tavakoli-Hoseini, N. (2011). Carbon-based solid acid catalyzed one-pot mannich reaction: A facile synthesis of β-amino carbonyl compounds. Bulletin of the Korean Chemical Society, 32, 635–638. doi:10.5012/bkcs.2011.32.2.635
   Google Scholar
• Davoodnia, A., Zare-Bidaki, A., & Behmadi, H. (2012). A rapid and green method for solvent-free synthesis of 1,8-dioxodecahydroacridines using tetrabutylammonium hexatungstate as a reusable heterogeneous catalyst. Chinese Journal of Catalysis, 33, 1797–1801. doi:10.1016/S1872-2067(11)60449-X
   Google Scholar
• Dehghan, M., Davoodnia, A., Bozorgmehr, M. R., & Bamoharram, F. F. (2016). Synthesis, characterization and application of two novel sulfonic acid functionalized ionic liquids as efficient catalysts in the synthesis of 1,8-dioxo-octahydroxanthenes. Heterocyclic Letters, 6, 251–257.
   Google Scholar
• Dingermann, T., Steinhilber, D., & Folkers, G. (2004). In molecular biology in medicinal chemistry. Weinheim: Wiley-VCH.
   Google Scholar
• Dömling, A. (2006). Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chemical Preview, 106, 17–89. doi:10.1021/cr0505728
   Google Scholar
• Eshghi, H., & Gordi, Z. (2003). An easy method for the generation of amides from ketones by a beckmann type rearrangement mediated by microwave. Synthetic Communications, 33, 2971–2978. doi:10.1081/SCC-120022469
   Google Scholar
• Eshghi, H., & Hassankhani, A. (2006). P2O5/SiO2-catalyzed one-pot synthesis of amides from ketones via schmidt reaction under microwave irradiation in dry media. Synthetic Communications, 36, 2211–2216. doi:10.1080/00397910600638978
   Google Scholar
• Eshghi, H., & Hassankhani, A. (2012). Phosphorus pentoxide supported on silica gel and alumina (P2O5/SiO2, P2O5/Al2O3) as useful catalysts in organic synthesis. Journal of the Iranian Chemical Society, 9, 467–482. doi:10.1007/s13738-011-0057-0
   Google Scholar
• Eshghi, H., Rafei, M., & Karimi, M. H. (2001). Document P2O5/SiO2 as an efficient reagent for esterification of phenols in dry media. Synthetic Communications, 31, 771–774. doi:10.1081/SCC-100103268
   Google Scholar
• Eshghi, H., Rafie, M., Gordi, Z., & Bohloli, M. (2003). Improvement of selectivity in the Fries rearrangement and direct acylation reactions by means of P2O5/SiO2 under microwave irradiation in solvent-free media. Journal of Chemical Research, 763–764. doi:10.3184/030823503772913674
   Google Scholar
• Eshghi, H., Rahimizadeh, M., Ghadamyari, Z., & Shiri, A. (2012). P2O5/SiO2 as an efficient and mild catalyst for trimethylsilylation of alcohols using hexamethyldisilazane. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42, 1435–1439. doi:10.1080/15533174.2012.682686
   Google Scholar
• Ghashang, M. (2014). Preparation of methyl/benzyl(2-hydroxynaphthalen-1-yl)(aryl)methylcarbamate derivatives using magnesium hydrogen sulfate. Research on Chemical Intermediates, 40, 1357–1364. doi:10.1007/s11164-013-1044-0
   Google Scholar
• Gholipour, S., Davoodnia, A., & Nakhaei-Moghaddam, M. (2015). Synthesis, characterization, and antibacterial evaluation of new alkyl 2-amino-4-aryl-4H-chromene-3-carboxylates. Chemistry of Heterocyclic Compounds, 51, 808–813. doi:10.1007/s10593-015-1779-1
   Google Scholar
• Habibi, D., Nasrollahzadeh, M., Mehrabi, L., & Mostafaee, S. (2013). P2O5-SiO2 as an efficient heterogeneous catalyst for the solvent-free synthesis of 1-substituted 1H-1,2,3,4-tetrazoles under conventional and ultrasound irradiation conditions. Monatshefte für Chemie - Chemical Monthly, 144, 725–728. doi:10.1007/s00706-012-0871-9
   Google Scholar
• Hajipour, A. R., & Ruoho, A. E. (2005). Nitric acid in the presence of P2O5 supported on silica gel—a useful reagent for nitration of aromatic compounds under solvent-free conditions. Tetrahedron Letters, 46, 8307–8310. doi:10.1016/j.tetlet.2005.09.178
   Google Scholar
• Hajipour, A. R., Zarei, A., Khazdooz, L., Pourmousavi, S. A., Mirjalili, B. F., & Ruoho, A. E. (2005). Direct sulfonylation of aromatic rings with aryl or alkyl sulfonic acid using supported P2O5/Al2O3. Phosphorus, Sulfur and Silicon and the Related Elements, 180, 2029–2034. doi:10.1080/104265090902796
   Google Scholar
• Hasaninejad, A., Zare, A., Balooty, L., Mehregan, H., & Shekouhy, M. (2010). Solvent-free, cross-aldol condensation reaction using silica-supported, phosphorus-containing reagents leading to α, α′-Bis(arylidene) cycloalkanones. Synthetic Communications, 40, 3488–3495. doi:10.1080/00397910903457282
   Google Scholar
• Hasaninejad, A., Zare, A., Sharghi, H., Niknam, K., & Shekouhy, M. (2007). P2O5/SiO2 as an efficient, mild, and heterogeneous catalytic system for the condensation of indoles with carbonyl compounds under solvent-free conditions. Arkivoc, 14, 39–50.
   Google Scholar
• Khashi, M., Davoodnia, A., & Prasada Rao Lingam, V. S. (2015). DMAP catalyzed synthesis of some new pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines. Research on Chemical Intermediates, 41, 5731–5742. doi:10.1007/s11164-014-1697-3
   Google Scholar
• Kumar, S., Aggarwal, R., Kumar, V., Sadana, R., Patel, B., Kaushik, P., & Kaushik, D. (2016). Solvent-free synthesis of bacillamide analogues as novel cytotoxic and anti-inflammatory agents. European Journal of Medicinal Chemistry, 123, 718–726. doi:10.1016/j.ejmech.2016.07.033
   Google Scholar
• Kundu, D., Majee, A., & Hajra, A. (2010). Zwitterionic-type molten salt: An efficient mild organocatalyst for synthesis of 2-amidoalkyl and 2-carbamatoalkyl naphthols. Catalysis Communications, 11, 1157–1159. doi:10.1016/j.catcom.2010.06.001
   Google Scholar
• Massah, A. R., Dabagh, M., Shahidi, S., Javaherian Naghash, H., Momeni, A. R., & Aliyan, H. (2009). P2O5/SiO2 as an efficient and recyclable catalyst for N-Acylation of sulfonamides under heterogeneous and solvent-free conditions. Journal of the Iranian Chemical Society, 6, 405–411. doi:10.1007/BF03245851
   Google Scholar
• Meerakrishna, R. S., Periyaraja, S., & Shanmugam, P. (2016). Copper-Catalyzed Multicomponent Synthesis of Fluorescent 2′-Phenyl-1′H-spiro[fluorene-9,4′-naphtho[2,3-h]quinoline]-7′,12′-dione Derivatives. European Journal of Organic Chemistry, 2016, 4516–4525. doi:10.1002/ejoc.201600647
   Google Scholar
• Mirjalili, B. F., Zolfigol, M. A., Bamoniri, A., Amrollahi, M. A., & Hazar, A. (2004). An efficient procedure for acetalization of carbonyl compounds with P2O5/SiO2. Phosphorus, Sulfur and Silicon and the Related Elements, 179, 1397–1401. doi:10.1080/10426500490463583
   Google Scholar
• Moghaddas, M., Davoodnia, A., Heravi, M. M., & Tavakoli-Hoseini, N. (2012). Sulfonated carbon catalyzed biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones. Chinese Journal of Catalysis, 33, 706–710. doi:10.1016/S1872-2067(11)60377-X
   Google Scholar
• Mohammadizadeh, M. R., Hasaninejad, A., Bahramzadeh, M., & Sardari Khanjarlou, Z. (2009). P2O5/SiO2 as a new, efficient, and reusable catalyst for preparation of β-enaminones under solvent-free conditions. Synthetic Communications, 39, 1152–1165. doi:10.1080/00397910802513052
   Google Scholar
• Naeimi, H., Sharghi, H., Salimi, F., & Rabiei, Kh. (2008). Facile and efficient method for preparation of schiff bases catalyzed by P2O5/SiO2 under free solvent conditions. Heteroatom Chemistry, 19, 43–47. doi:10.1002/hc.20383
   Google Scholar
• Nakhaei, A., & Davoodnia, A. (2014). Application of a Keplerate type giant nanoporous isopolyoxomolybdate as a reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles. Chinese Journal of Catalysis, 35, 1761–1767. doi:10.1016/S1872-2067(14)60174-1
   Google Scholar
• Nakhaei, A., Yadegarian, S., & Davoodnia, A. (2016). Efficient and rapid hantzsch synthesis of1,4-dihydropyridines using a nano isopolyoxomolybdate as a reusable catalyst under solvent-free condition. Heterocyclic Letters, 6, 429–439.
   Google Scholar
• Shafiee, M. R. M., Moloudi, R., & Ghashang, M. (2011). Document Preparation of methyl (2-hydroxynaphthalen-1-yl)(aryl)methyl/ benzylcarbamate derivatives using magnesium (II) 2,2,2-trifluoroacetate as an efficient catalyst. Journal of Chemical Research, 622–625. doi:10.3184/174751911X13182405888457
   Google Scholar
• Shaterian, H. R., & Hosseinian, A. (2014). Efficient synthesis of 1-carbamatoalkyl-2-naphthols using Brønsted acidic ionic liquid as reusable catalyst. Research on Chemical Intermediates, 40, 3011–3019. doi:10.1007/s11164-013-1147-7
   Google Scholar
• Shaterian, H. R., Hosseinian, A., & Ghashang, M. (2009). PPA-SiO2 catalyzed multi-component synthesis of n-[α-(β-hydroxy-α-naphthyl)(benzyl)] o-alkyl carbamate derivatives. Chinese Journal of Chemistry, 27, 821–824. doi:10.1002/cjoc.200990137
   Google Scholar
• Shaterian, H. R., Ranjbar, M., & Azizi, K. (2011). Efficient multi-component synthesis of highly substituted imidazoles utilizing P2O5/SiO2 as a reusable catalyst. Chinese Journal of Chemistry, 29, 1635–1645. doi:10.1002/cjoc.201180293
   Google Scholar
• Shen, A. Y., Tsai, C. T., & Chen, C. L. (1999). Synthesis and cardiovascular evaluation of N-substituted 1- aminomethyl-2-naphthols. European Journal of Medicinal Chemistry, 34, 877–882. doi:10.1016/S0223-5234(99)00204-4
   Google Scholar
• Slobbe, P., Ruijter, E., & Orru, R. V. A. (2012). Recent applications of multicomponent reactions in medicinal chemistry. MedChemComm, 3, 1189–1218. doi:10.1039/c2md20089a
   Google Scholar
• Song, Z. G., Sun, X. H., Liu, L. L., & Cui, Y. (2013). Efficient one-pot synthesis of 1-carbamatoalkyl-2-naphthols using aluminum methanesulfonate as a reusable catalyst. Research on Chemical Intermediates, 39, 2123–2131. doi:10.1007/s11164-012-0744-1
   Google Scholar
• Song, Z., Liu, L., Sun, X., & Cui, Y. (2014). Copper chloride-catalyzed efficient three-component one-pot synthesis of carbamatoalkyl naphthols under solvent-free conditions. Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 53B, 740–745.
   Google Scholar
• Taghavi-Khorasani, F., & Davoodnia, A. (2015). A fast and green method for synthesis of tetrahydrobenzo[a]xanthene-11-ones using Ce(SO4)2·4H2O as a novel, reusable, heterogeneous catalyst. Research on Chemical Intermediates, 41, 2415–2425. doi:10.1007/s11164-013-1356-0
   Google Scholar
• Tamaddon, F., Khoobi, M., & Keshavarz, E. (2007). (P2O5/SiO2): A useful heterogeneous alternative for the Ritter reaction. Tetrahedron Letters, 48, 3643–3646. doi:10.1016/j.tetlet.2007.03.134
   Google Scholar
• Thompson, L. A. (2000). Recent applications of polymer-supported reagents and scavengers in combinatorial, parallel, or multistep synthesis. Current Opinion in Chemical Biology, 4, 324–337. doi:10.1016/S1367-5931(00)00096-X
   Google Scholar
• Touré, B. B., & Hall, D. G. (2009). Natural product synthesis using multicomponent reaction strategies. Chemical Reviews, 109, 4439–4486. doi:10.1021/cr800296p
   Google Scholar
• Wang, M., Liu, Y., Song, Z., & Zhao, S. (2013). A convenient three-component synthesis of carbamatoalkyl naphthols catalyzed by cerium ammonium nitrate. Bulletin of the Chemical Society of Ethiopia, 27, 421–426. doi:10.4314/bcse.v27i3.11
   Google Scholar
• Wang, M., Wang, Q. L., Zhao, S., & Wan, X. (2013). Solvent-free one-pot synthesis of 1-carbamatoalkyl-2-naphthols by a tin tetrachloride catalyzed multicomponent reaction. Monatshefte für Chemie - Chemical Monthly, 144, 975–980. doi:10.1007/s00706-013-0927-5
   Google Scholar
• Wu, L., & Wang, X. (2011). P2O5/SiO2 as a new, efficient and reusable catalyst for preparation of 4,4’-epoxydicoumarins under solvent-free conditions. E-Journal of Chemistry, 8, 1626–1631. doi:10.1155/2011/849795
   Google Scholar
• Yang, J. M., Jiang, C. N., Dong, H., & Fang, D. (2013). Synthesis of 1-carbamatoalkyl-2-naphthols in Tween® 20 aqueous micelles. Journal of Chemical Research, 279–281. doi:10.3184/174751913X13647554585207
   Google Scholar
• Zare, A., Yousofi, T., & Moosavi-Zare, A. R. (2012). Ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate: A novel and highly efficient catalyst for the preparation of 1-carbamatoalkyl-2-naphthols and 1-amidoalkyl-2-naphthols. RSC Advances, 2, 7988–7991. doi:10.1039/c2ra20679j
   Google Scholar