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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 16
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Articles

Carbon-SO3H: An efficient catalyst for the synthesis of biscoumarin under ambient reaction conditions and their in silico studies

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Pages 2440-2460 | Received 20 Mar 2020, Published online: 26 Jun 2020

References

  • Bryan, M. C.; Dunn, P. J.; Entwistle, D.; Gallou, F.; Koenig, S. G.; Hayler, J. D.; Hickey, M. R.; Hughes, S.; Kopach, M. E.; Moine, G.; et al. Green Chem. 2018, 20, 5082–5103. DOI: 10.1039/C8GC01276H.
  • Ehlers, D.; Pfister, M.; Gerard, D.; Quirin, K. W.; Bork, W. R.; Nadolny, P. T. Int. J. Food Sci. Tech. 1996, 31, 91–95. DOI: 10.1111/j.1365-2621.1996.19-319.x.
  • Manolov, I.; Maichle‐Moessmer, C.; Nicolova, I.; Danchev, N. Arch. Pharm. 2006, 339, 319–326. DOI: 10.1002/ardp.200500149.
  • Abid, O.-U.-R.; Babar, T. M.; Ali, F. I.; Ahmed, S.; Wadood, A.; Rama, N. H.; Uddin, R.; Ul-Haq, Z.; Khan, A.; Choudhary, M. I. ACS Med. Chem. Lett. 2010, 1, 145. DOI: 10.1021/ml100068u.
  • Ibrar, A.; Zaib, S.; Khan, I.; Jabeen, F.; Iqbal, J.; Saeed, A. RSC Adv. 2015, 5, 89919–89931. DOI: 10.1039/C5RA14900B.
  • Asgari, M. S.; Mohammadi-Khanaposhtani, M.; Kiani, M.; Ranjbar, P. R.; Zabihi, E.; Pourbagher, R.; Rahimi, R.; Faramarzi, M. A.; Biglar, M.; Larijani, B.; et al. Bioorg. Chem. 2019, 92, 103206. DOI: 10.1016/j.bioorg.2019.103206.
  • Li, J.; Meng, J. R.; Qu, D.; Zhang, Z.-D.; Li, F.; Yang, X. H.; Luo, X.-X.; Li, J.-T.; Li, M.-K. Res. Chem. Intermed. 2015, 41, 8257–8267. DOI: 10.1007/s11164-014-1889-x.
  • Faisal, M.; Saeed, A.; Shahzad, D.; Fattah, T. A.; Lal, B.; Channar, P. A.; Mahar, J.; Saeed, S.; Mahesar, P. A.; Larik, F. A. Eur. J. Med. Chem. 2017, 141, 386–403. DOI: 10.1016/j.ejmech.2017.10.009.
  • Su, C.-X.; Mouscadet, J.-F.; Chiang, C.-C.; Tsai, H.-J.; Hsu, L.-Y. Chem. Pharm. Bull. 2006, 54, 682–686. DOI: 10.1248/cpb.54.682.
  • Perumalsamy, H.; Sankarapandian, K.; Veerappan, K.; Natarajan, S.; Kandaswamy, N.; Thangavelu, L.; Balusamy, S. R. Phytomedicine 2018, 46, 119–130. DOI: 10.1016/j.phymed.2018.04.021.
  • Samija, M.; Elma, V.; Amar, O.; Jasmina, E.; Haris, N.; Hurija, D.; Davorka, Z. IFMBE Proceedings; Springer: Singapore, 2017.
  • Mayank, A.; Singh, N.; Kaur, N.; Garg, N.; Singh, N. Comput. Bio. Chem. 2019, 83, 107104. DOI: 10.1016/j.compbiolchem.2019.107104.
  • Zhang, H.; Luo, Q.; Mao, Y.; Zhao, Y.; Yu, T. J. Photochem. Photobiol. A Chem. 2017, 346, 10–16. DOI: 10.1016/j.jphotochem.2017.05.039.
  • Narendran, K.; Nanthini, R. New J. Chem. 2015, 39, 4948–4956. DOI: 10.1039/C5NJ00322A.
  • Pramod, A. G.; Nadaf, Y. F.; Renuka, C. G.; Sucheta, M. Biscoumarin derivative for designing the WLED display applications. AIP Conference Proceedings 2115, Hisar, Haryana, India, July 12, 2019. https://doi.org/10.1063/1.5113045.
  • Marek, K.; Cławski, W.; Jakěsov´ Charyton, M. M.; Demitri, N.; Koszarna, B.; Oppelt, K.; Sariciftci, S.; Gryko, D. T.; Głowacki, E. D. J. Mater. Chem. A. 2017, 5, 20780–20788. DOI: 10.1039/C7TA05882A.
  • Rahmani, S.; Zeynizadeh, B. Res. Chem. Intermed. 2019, 45, 1227–1248. DOI: 10.1007/s11164-018-3671-y.
  • Gandhi, D.; Agarwal, S. J. Heterocyclic Chem. 2018, 55, 2977–2984. DOI: 10.1002/jhet.3384.
  • Agarwal, S.; Agarwal, D. K.; Gandhi, D.; Goyal, K.; Goyal, P. Lett. Org. Chem. 2018, 15, 863–869. DOI: 10.2174/1570178615666180326161710.
  • Shahzad, D.; Saeed, A.; Faisal, M.; Larik, F. A.; Bilquees, S.; Channar, P. A. Org. Prep. Proced. Int. 2019, 51, 199–239. DOI: 10.1080/00304948.2019.1599788.
  • Mahmoodi, N. O.; Pirbasti, F. G.; Jalalifar, Z. J. Chin. Chem. Soc. 2018, 65, 383–394. DOI: 10.1002/jccs.201700363.
  • Abramovitch, R. A.; Gear, J. R. Can. J. Chem. 1958, 36, 151–1510. DOI: 10.1139/v58-019.
  • Shirini, F.; Abedini, M.; Zamani, S.; Moafi, H. F. J. Nanostruct. Chem. 2015, 5, 123–130. DOI: 10.1007/s40097-014-0143-9.
  • Abbasi, F.; Azizi, N.; Abdoli-Senejani, M. J. Iran. Chem. Soc. 2017, 14, 2097–2103. DOI: 10.1007/s13738-017-1146-5.
  • Yang, C.; Su, W. Q.; Xu, D. Z. RSC Adv. 2016, 6, 99656–99663. DOI: 10.1039/C6RA23018K.
  • Kauthale, S. S.; Tekale, S. U.; Jadhav, K. M.; Pawar, R. P. Mol. Divers. 2016, 20, 763–770. DOI: 10.1007/s11030-016-9673-z.
  • Maleki, B. Org. Prep. Proced. Int. 2016, 48, 303–318. DOI: 10.1080/00304948.2016.1165061.
  • Mayank, M.; Singh, A.; Raj, P.; Kaur, R.; Singh, A.; Kaur, N.; Singh, N. New J. Chem. 2017, 41, 3872–3881. DOI: 10.1039/C6NJ03763A.
  • Safaei-Ghomi, J.; Eshteghal, F.; Shahbazi-Alavi, H. Polycyclic Aromat. Compd. 2017, 40, 13–20. doi.org/ DOI: 10.1080/10406638.2017.1348368..
  • Azizi, N.; Abbasi, F.; Abdoli-Senejani, M. Chem. Sel. 2018, 3, 3797–3802. DOI: 10.1002/slct.201800138.
  • Brahmachari, G.; Begam, S. Chem. Sel. 2019, 4, 5414.
  • Daneshvar, N.; Goli-Jolodar, O.; Karimi-Chayjani, R.; Langarudi, M. S. N.; Shirini, F. Sustainable and Eco‐Friendly Method for the Synthesis of Some Bioactive Derivatives of Biscoumarin and Pyrano[3,2‐c ]Chromene‐3‐Carbonitrile Using Taurine, as the Catalyst. Chem. Sel. 2019, 4, 1562–1566. DOI: 10.1002/slct.201803210.
  • Faisal, M.; Larik, F. A.; Saeed, A. J. Porous Mater. 2019, 26, 455–466. DOI: 10.1007/s10934-018-0625-0.
  • Mathavan, S.; Kannan, K.; Yamajal, R. B. R. D. Org. Biomol. Chem. 2019, 17, 9620–9626. DOI: 10.1039/c9ob02090j.
  • Zhu, A.; Bai, S.; Li, L.; Wang, M.; Wang, J. Catal. Lett. 2015, 145, 1089–1093. DOI: 10.1007/s10562-015-1487-6.
  • Hamdi, N.; Puerta, M. C.; Valerga, P. Eur. J. Med. Chem. 2008, 43, 2541–2548. DOI: 10.1016/j.ejmech.2008.03.038.
  • Singh, P.; Kumar, P.; Katyal, A.; Kalra, R.; Dass, S. K.; Prakash, S.; Chandra, R. Catal. Lett. 2010, 134, 303–308. DOI: 10.1007/s10562-009-0239-x.
  • Montazeri, N.; Vahabi, V. Bulg. Chem. Commun. 2015, 47, 136.
  • Kiasat, A. R.; Hemat-Alian, L. Res. Chem. Intermed. 2015, 41, 873–880. DOI: 10.1007/s11164-013-1239-4.
  • Shirini, F.; Khaligh, N. G. Chin. J. Catal. 2013, 34, 1890–1896. DOI: 10.1016/S1872-2067(12)60669-X.
  • Tabatabaeian, K.; Heidari, H.; Khorshidi, A.; Mamaghani, M.; Mahmoodi, N. O. J. Serb. Chem. Soc. 2012, 77, 407–413. DOI: 10.2298/JSC110427189T.
  • Vahabi, V.; Hatamjafari, F. Orient. J. Chem. 2014, 30, 853–855. DOI: 10.13005/ojc/300263.
  • Seddighi, M.; Shirini, F.; Mamaghani, M. RSC Adv. 2013, 3, 24046. DOI: 10.1039/c3ra44053b.
  • Rezaei, R.; Sheikhi, M. R. Res. Chem. Intermed. 2015, 41, 1283–1292. DOI: 10.1007/s11164-013-1272-3.
  • Niknama, K.; Sajadi, S. A.; Hosseini, R.; Baghernejad M. Iran. J. Catal. 2014, 4, 163.
  • Sedighi, M.; Montazeri, N. Adv. Stud. Biol. 2015, 7, 89–95. DOI: 10.12988/asb.2015.41160.
  • Iravani, N.; Keshavarz, M.; Mousavi, M.; Baghernejad, M. Iran. J. Catal. 2015, 5, 65.
  • Ghorbani, F.; Pourmousavi, S. A.; Kiyani, H. Curr. Organocat. 2019, 7, 55–80. DOI: 10.2174/2213337206666190717164606.
  • Teli, P.; Sethiya, A.; Agarwal, S. An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives. Chem. Sel. 2019, 4, 13772–13787. DOI: 10.1002/slct.201903632.
  • Karnakar, K.; Murthy, S. N.; Kumar, R.; Nageswar, Y. V. D.; Reddy, T. V. K.; Bethala, B. L. A.; Devi, P.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1968.
  • Ramesh, R.; Sankar, G.; Malecki, J. G.; Appaswami, L. J. Iran. Chem. Soc. 2018, 15, 1–9. DOI: 10.1007/s13738-017-1202-1.
  • Zhang, H.; Wang, W.; Zhang, B.; Li, H.; Zhang, Q. RSC Adv. 2016, 6, 30956–30962. DOI: 10.1039/C6RA01680D.
  • Karnakar, K.; Murthy, S. N.; Ramesh, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Chandrakala, U.; Devi, B. L. A. P.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 3497–3501. DOI: 10.1016/j.tetlet.2012.04.122.
  • Singh, R.; Ganaie, S. A.; Singh, A.; Chaudhary, A. Synth. Commun. 2019, 49, 80–93. DOI: 10.1080/00397911.2018.1542003.
  • Avdović, E. H.; Milenković, D.; Marković, J. M.; Đorović, J.; Vuković, N.; Vukić, M. D.; Jevtić, V. V.; Trifunović, S. R.; Potočňák, I.; Marković, Z. Spectrochim Acta A Mol Biomol Spectrosc. 2018, 195, 31–40. DOI: 10.1016/j.saa.2018.01.023.
  • Kaur, P.; Chamberlin, A. R.; Poulos, T. L.; Sevrioukova, I. F. J. Med. Chem. 2016, 59, 4210–4220. DOI: 10.1021/acs.jmedchem.5b01146.
  • Froese, D. S.; Kopec, J.; Rembeza, E.; Bezerra, G. A.; Oberholzer, A. E.; Suormala, T.; Lutz, S.; Chalk, R.; Borkowska, O.; Baumgartner, M. R.; et al. Nat. Commun. 2018, 9, 2261. DOI: 10.1038/s41467-018-04735-2.
  • Xu, L.; Liu, H.; Murray, B. P.; Callebaut, C.; Lee, M. S.; Hong, A.; Strickley, R. G.; Tsai, L. K.; Stray, K. M.; Wang, Y.; et al. ACS Med. Chem. Lett. 2010, 1, 209–213. DOI: 10.1021/ml1000257.
  • Stankova, J.; Lawrance, A.; Rozen, R. Curr. Pharm. Des. 2008, 14, 1143–1150. DOI: 10.2174/138161208784246171.
  • Devi, B. L. A. P.; Gangadhar, K. N.; Prasad, P. S. S.; Jagannadh, B.; Prasad, R. B. N. ChemSusChem. 2009, 2, 617–620. DOI: 10.1002/cssc.200900097.
  • Devi, B. L. A. P.; Gangadhar, K. N.; Siva Kumar, K. L. N.; Shiva Shanker, K.; Prasad, R. B. N.; Sai Prasad, P. S. J. Mol. Catal. A. Chem. 2011, 345, 96–100. DOI: 10.1016/j.molcata.2011.05.025.
  • Estes, C. S.; Gerard, A. Y.; Godward, J. D.; Hayes, S. B.; Liles, S. H.; Shelton, J. L.; Stewart, T. S.; Webster, R. I.; Webster, H. F. Carbon. 2019, 142, 547–557. DOI: 10.1016/j.carbon.2018.10.074.
  • Kong, P. S.; Aroua, M. K.; Daud, W. M. A. W.; Lee, H. V.; Cognet, P.; Peres, Y. RSC Adv. 2016, 6, 68885–68905. DOI: 10.1039/C6RA10686B.
  • Liu, F.; Sun, J.; Zhu, L.; Meng, X.; Qi, C.; Xiao, F.-S. J. Mater. Chem. 2012, 22, 5495. DOI: 10.1039/c2jm16608a.
  • Lee, D. Molecules 2013, 18, 8168–8180. DOI: 10.3390/molecules18078168.
  • Gong, G.-X.; Zhou, J.-F.; An, L.-T.; Duan, X.-L.; Ji, S.-J. Synth. Commun. 2009, 39, 497–505. DOI: 10.1080/00397910802398272.
  • Constable, D. J.; Curzons, A. D.; Cunningham, V. L. Green Chem. 2002, 4, 521–527. DOI: 10.1039/B206169B.
  • Bahuguna, A.; Kumar, S.; Sharma, V.; Reddy, K. L.; Bhattacharyya, K.; Kumar, P. C. R.; Krishnan, V. ACS Sustainable Chem. Eng. 2017, 5, 8551–8567. DOI: 10.1021/acssuschemeng.7b00648.
  • Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. J. Mol. Biol. 1996, 261, 470–489. DOI: 10.1006/jmbi.1996.0477.
  • Kramer, B.; Rarey, M.; Lengauer, T. Proteins 1997, 29, 221–225. DOI: 10.1002/(SICI)1097-0134(1997)1+<221::AID-PROT30>3.0.CO;2-O.
  • LeadIt, version 2.1.8, BioSolveIT GmbH. BioSolveIT: Sankt Augustin, Germany.
  • Böhm, H.-J. J. Comput. Aided Mol. Des. 1994, 8, 243–256. DOI: 10.1007/BF00126743.
  • SYBYL, TRIPOS Associates Inc.: St. Louis, MO, 1994.
  • Discovery Studio, version 4.0, Accelrys Software, Inc.: San Diego, CA, www.accelrys.com/products/collaborativescience/biovia-discovery-studio/
  • Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S. A.; Karplus, M. J. Comput. Chem. 1983, 4, 187–217. DOI: 10.1002/jcc.540040211.
  • Bietz, S.; Urbaczek, S.; Schulz, B.; Rarey, M. J. Cheminform. 2014, 6, 12. DOI: 10.1186/1758-2946-6-12.
  • Stierand, K.; Rarey, M. ACS Med. Chem. Lett. 2010, 1, 540–545. DOI: 10.1021/ml100164p.

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