Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis and Characterization of Pine-cone Derived Carbon-based Solid Acid: a Green and Recoverable Catalyst for the Synthesis of Pyrano_ pyrazole, Amino-benzochromene, Amidoalkyl Naphthol and Thiazolidinedione Derivatives

Author(s): Fatemeh Ghorbani, Seied Ali Pourmousavi* and Hamzeh Kiyani

Volume 18, Issue 1, 2021

Published on: 10 February, 2020

Page: [66 - 81] Pages: 16

DOI: 10.2174/1570178617666200210105635

Price: $65

Abstract

In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180°C in a sealed autoclave in a one-step procedure. The resulted Nanocatalyst was characterized by FT-IR, TGA, XRD, FE-SEM and elemental analysis (EA). The result of characterization was shown that the carbon-based acid is amorphous with polycyclic aromatic carbon sheets attached plentiful -OH, -COOH, and -SO3H groups. The catalytic activities of Pine-SO3H was investigated in the highly efficient synthesis of pyrano[2,3-c] pyrazole, amino-benzochromenes, amidoalkyl naphthol and 5-arylidene-2,4-thiazolidinedione derivatives. The application of Pine-SO3H in the synthesis offers several advantages such as simple procedure with an easy work-up, recoverable catalyst, mild condition, eco-friendliness, excellent yields, short reaction times and use of an inexpensive catalyst.

Keywords: Catalyst, pyrano[2, 3-c] pyrazole, amino-benzochromenes, Carbon-based solid acid, Biomass, Pine-Cones, amidoalkyl naphthol, 5-arylidene-2, 4-thiazolidinedione derivatives.

« Previous
Graphical Abstract

[1]
Okamura, M.; Takagaki, A.; Toda, M. Chem. Mater., 2006, 18, 3039-3045.
[http://dx.doi.org/10.1021/cm0605623]
[2]
Dora, S.; Bhaskar, T.; Singh, R.; Naik, D.V.; Adhikari, D.K. Bioresour. Technol., 2012, 120, 318-321.
[http://dx.doi.org/10.1016/j.biortech.2012.06.036] [PMID: 22776237]
[3]
Xu, Q.; Wang, Y.J.; Yin, D.L. Front. Chem. Sci. Eng., 2009, 3, 201-205.
[http://dx.doi.org/10.1007/s11705-009-0052-5]
[4]
Lai, B. ACS Sustain. Chem.& Eng., 2018, 6, 17076-17086.
[http://dx.doi.org/10.1021/acssuschemeng.8b04451]
[5]
Chen, G.; Fang, B. Bioresour. Technol., 2011, 102(3), 2635-2640.
[http://dx.doi.org/10.1016/j.biortech.2010.10.099] [PMID: 21067915]
[6]
Jun, T.Y.; Arumugam, S.D.; Latip, N.H.A. Environ. Asia, 2012, 3, 143-148.
[7]
Zeng, D.; Liu, S.; Gong, W. Appl. Catal. A., 2014, 469, 284-289.
[http://dx.doi.org/10.1016/j.apcata.2013.09.038]
[8]
Chen, H.Y.; Cui, Z.W. Catalysis., 2016, 6, 211-216.
[9]
Lai, Y.; Liu, W.; Fang, J. Adv., 2015, 5, 93676-93683.
[10]
Liu, T.; Li, Z.; Li, W.; Shi, C.; Wang, Y. Bioresour. Technol., 2013, 133, 618-621.
[http://dx.doi.org/10.1016/j.biortech.2013.01.163] [PMID: 23453798]
[11]
Wankhade Amey, A.; Ganvir, V.N. Sci., 2013, 2(4), 53-55.
[12]
Suganuma, S.; Nakajima, K.; Kitano, M.; Yamaguchi, D.; Kato, H.; Hayashi, S.; Hara, M. J. Am. Chem. Soc., 2008, 130(38), 12787-12793.
[http://dx.doi.org/10.1021/ja803983h] [PMID: 18759399]
[13]
Ayrilmis, N.; Buyuksari, U.; Avci, E. For. Ecol. Manage., 2009, 259, 65-70.
[http://dx.doi.org/10.1016/j.foreco.2009.09.043]
[14]
Micales, J.A. J.L. Springer, 1994, 3, 17-26.
[15]
Momčilović, M.; Purenović, M.; Bojić, A. Desalination, 2011, 276, 53-59.
[http://dx.doi.org/10.1016/j.desal.2011.03.013]
[16]
Özhan, A.; Sahin, Ö.; Küçük, M.M. Cellulose, 2014, 21, 2457-2467.
[http://dx.doi.org/10.1007/s10570-014-0299-y]
[17]
Nunell, G.V.; Fernandez, M.E.; Bonelli, P.R.; Cukierman, A.L. J. Colloid Interface Sci., 2015, 440, 102-108.
[http://dx.doi.org/10.1016/j.jcis.2014.10.058] [PMID: 25460695]
[18]
Ofomaja, A.E.; Naidoo, E.B. Chem. Eng. J., 2011, 175, 260-270.
[http://dx.doi.org/10.1016/j.cej.2011.09.103]
[19]
Shu, Q.; Gao, J.Z. Appl. Energy, 2010, 87, 2589-2596.
[http://dx.doi.org/10.1016/j.apenergy.2010.03.024]
[20]
Zong, M.H.; Duan, Z.Q.; Lou, W.Y. Green Chem., 2007, 9, 434-437.
[http://dx.doi.org/10.1039/b615447f]
[21]
Mirkhani, V.; Moghadam, M.; Tangestaninejad, S. Monatsh. Chem., 2010, 140, 1489-1494.
[http://dx.doi.org/10.1007/s00706-009-0213-8]
[22]
Mistry, P.T.; Kamdar, N.R.; Haveliwala, D.D. J. Heterocycl. Chem., 2012, 49, 349-357.
[http://dx.doi.org/10.1002/jhet.700]
[23]
Kuo, S.C.; Huang, L.J.; Nakamura, H. J. Med. Chem., 1984, 27(4), 539-544.
[http://dx.doi.org/10.1021/jm00370a020] [PMID: 6708056]
[24]
Ahluwalia, V.K.; Dahiya, A.; Garg, V. Indian J. Chem., 1997, 36, 88-90.
[25]
Zaki, M.E.A.; Morsy, E.M.; Abdel-Motti, F.M. Heterocycl. Commun., 2004, 10, 97-102.
[http://dx.doi.org/10.1515/HC.2004.10.1.97]
[26]
Mandha, S.R.; Siliveri, S.; Alla, M.; Bommena, V.R.; Bommineni, M.R.; Balasubramanian, S. Bioorg. Med. Chem. Lett., 2012, 22(16), 5272-5278.
[http://dx.doi.org/10.1016/j.bmcl.2012.06.055] [PMID: 22818081]
[27]
Abdelrazek, F.M.; Michael, F.A. Arch. Pharm. Chem. Sci., 2006, 339(6), 305-312.
[http://dx.doi.org/10.1002/ardp.200500259]
[28]
Ramiz, M.M.M.; Abdel Hafiz, I.S.; Abdel Reheim, M.A.M. J. Chin. Chem. Soc. (Taipei), 2012, 59, 72-80.
[http://dx.doi.org/10.1002/jccs.201100194]
[29]
Wamhoff, H.; Kroth, E.; Strauch, K. Synthesis, 2011, 1993(11), 1129-1132.
[http://dx.doi.org/10.1055/s-1993-26014]
[30]
Armetso, D.; Horspool, W.M.; Martin, N. J. Org. Chem., 1989, 54, 3069-3072.
[http://dx.doi.org/10.1021/jo00274a021]
[31]
Kiyani, H.; Samimi, H.A.; Ghorbani, F. Curr. Chem. Lett., 2013, 2, 197-206.
[http://dx.doi.org/10.5267/j.ccl.2013.07.002]
[32]
Reddy, M.B.M.; Pasha, M.A. Indian J. Chem., 2012, 51B, 537-541.
[33]
Babaie, M.; Sheibani, H. Arab. J. Chem., 2011, 4, 159-162.
[http://dx.doi.org/10.1016/j.arabjc.2010.06.032]
[34]
Vasuki, G.; Kandhasamy, K. Tetrahedron Lett., 2008, 49, 5636-5638.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.055]
[35]
Reddy, M.B.M.; Jayashankara, V.P.; Pasha, M.A. Synth. Commun., 2012, 40, 2930-2934.
[http://dx.doi.org/10.1080/00397910903340686]
[36]
Poupaert, J.; Carato, P.; Colacino, E.; Yous, S. Curr. Med. Chem., 2005, 12(7), 877-885.
[http://dx.doi.org/10.2174/0929867053507388] [PMID: 15853716]
[37]
Kathrotiya, H.G.; Patel, M.P. Med. Chem. Res., 2012, 21, 3406-3416.
[http://dx.doi.org/10.1007/s00044-011-9861-4]
[38]
Abrunhosa, L.; Costa, M.; Areias, F.; Venâncio, A.; Proença, F. J. Ind. Microbiol. Biotechnol., 2007, 34(12), 787-792.
[http://dx.doi.org/10.1007/s10295-007-0255-z] [PMID: 17899234]
[39]
Kidwai, M.; Saxena, S.; Khan, M.K.R.; Thukral, S.S. Bioorg. Med. Chem. Lett., 2005, 15(19), 4295-4298.
[http://dx.doi.org/10.1016/j.bmcl.2005.06.041] [PMID: 16040241]
[40]
El-Agrody, A.M.; Fouda, A.M.; Al-Dies, A.A.M. Med. Chem. Res., 2014, 23, 3187-3199.
[http://dx.doi.org/10.1007/s00044-013-0904-x]
[41]
Narender, T.; Shweta, S.; Gupta, S. Bioorg. Med. Chem. Lett., 2004, 14(15), 3913-3916.
[http://dx.doi.org/10.1016/j.bmcl.2004.05.071] [PMID: 15225696]
[42]
C. Catal. Commun., 2008, 9, 1017-1020.
[43]
F. Res. Chem. Intermed., 2014, 68(8), 1104-1112.
[44]
Heravi, M.M.; Baghernejad, B.; Oskooie, H.A. J. Chin. Chem. Soc. (Taipei), 2008, 55, 3-7.
[45]
Kusakabe, Y.; Nagatsu, J.; Shibuya, M.; Kawaguchi, O.; Hirose, C. J. Antibiot. (Tokyo), 1972, 25(1), 44-47.
[http://dx.doi.org/10.7164/antibiotics.25.44] [PMID: 5010645]
[46]
Remillard, S.; Rebhun, L.I.; Howie, G.A.; Kupchan, S.M. Science, 1975, 189(4207), 1002-1005.
[http://dx.doi.org/10.1126/science.1241159] [PMID: 1241159]
[47]
Ren, H.; Grady, S.; Gamenara, D.; Heinzen, H.; Moyna, P.; Croft, S.L.; Kendrick, H.; Yardley, V.; Moyna, G. Bioorg. Med. Chem. Lett., 2001, 11(14), 1851-1854.
[http://dx.doi.org/10.1016/S0960-894X(01)00308-0] [PMID: 11459645]
[48]
Benedini, F.; Bertolini, G.; Cereda, R.; Donà, G.; Gromo, G.; Levi, S.; Mizrahi, J.; Sala, A. J. Med. Chem., 1995, 38(1), 130-136.
[http://dx.doi.org/10.1021/jm00001a018] [PMID: 7837224]
[49]
Peglion, J.L.; Vian, J.; Gourment, B. Bioorg. Med. Chem. Lett., 1997, 7, 881-886.
[http://dx.doi.org/10.1016/S0960-894X(97)00126-1]
[50]
Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyamoto, K.; Maruyama, N.; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T. J. Med. Chem., 1997, 40(1), 105-111.
[http://dx.doi.org/10.1021/jm9605288] [PMID: 9016334]
[51]
Knapp, S. Chem. Rev., 1995, 95, 1859-1876.
[http://dx.doi.org/10.1021/cr00038a006]
[52]
Shaterian, H.A.; Rigi, F. Res. Chem. Intermed., 2013, 40, 1859-1876.
[53]
Wang, M.; Liang, Y.; Zang, T.T. Chin. J. Chem., 2011, 29, 1660-1656.
[54]
Khodaei, M.M.; Khosropour, A.R.; Moghanian, H. Synlett, 2006, 6, 916-920.
[http://dx.doi.org/10.1055/s-2006-939034]
[55]
Shaterian, H.R.; Yarahmadi, H.; Ghashang, M. Bioorg. Med. Chem. Lett., 2008, 18(2), 788-792.
[http://dx.doi.org/10.1016/j.bmcl.2007.11.035] [PMID: 18053712]
[56]
Nagawade, R.R.; Shinde, D.B. Chin. J. Chem., 2007, 25, 1710-1714.
[http://dx.doi.org/10.1002/cjoc.200790316]
[57]
Kiyani, H.; Darbandi, H.; Mosallanezhad, A. Res. Chem. Intermed., 2014, 41, 7561-7579.
[http://dx.doi.org/10.1007/s11164-014-1844-x]
[58]
Pourmousavi, S.A.; Moghimi, P.; Ghorbani, F.; Zamani, M. J. Mol. Struct., 2017, 1144, 87-102.
[http://dx.doi.org/10.1016/j.molstruc.2017.05.010]
[59]
Oguchi, M.; Wada, K.; Honma, H.; Tanaka, A.; Kaneko, T.; Sakakibara, S.; Ohsumi, J.; Serizawa, N.; Fujiwara, T.; Horikoshi, H.; Fujita, T. J. Med. Chem., 2000, 43(16), 3052-3066.
[http://dx.doi.org/10.1021/jm990522t] [PMID: 10956213]
[60]
Malamas, M.S.; Sredy, J.; Gunawan, I.; Mihan, B.; Sawicki, D.R.; Seestaller, L.; Sullivan, D.; Flam, B.R. J. Med. Chem., 2000, 43(5), 995-1010.
[http://dx.doi.org/10.1021/jm990476x] [PMID: 10715163]
[61]
Murugan, R.; Anbazhagan, S. Lingeshwaran, Sriman Narayanan, S. Eur. J. Med. Chem., 2009, 44(8), 3272-3279.
[http://dx.doi.org/10.1016/j.ejmech.2009.03.035] [PMID: 19395129]
[62]
Shelke, K.F.; Sapkal, S.B.; Kakade, G.K. Green Chem. Lett. Rev., 2010, 3, 17-21.
[http://dx.doi.org/10.1080/17518250903478345]
[63]
Shelke, K.F.; Sapkal, S.B.; Niralwad, K.S. Eur. J. Chem., 2010, 8, 12-17.
[64]
Yang, B.Y.; Yang, D.H. J. Chem. Res., 2011, 35, 238-239.
[http://dx.doi.org/10.3184/174751911X13025104502362]
[65]
Mahalle, S.R.; Netankar, P.D.; Bondge, S.P. Green Chem. Lett. Rev., 2008, 1, 103-106.
[http://dx.doi.org/10.1080/17518250802139881]
[66]
Yang, H.; Yan, Y.; Liu, Y. J. Phys. Chem. B, 2004, 108(45), 17320-17328.
[http://dx.doi.org/10.1021/jp046948n]

Rights & Permissions Print Cite
Article Metrics
13
1
© 2024 Bentham Science Publishers | Privacy Policy