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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Green Synthesis of Benzoimidazopyrimidine, Benzimidazoloquinazolinone, Triazolopyrimidine and Triazoloquinazolinone Derivatives Catalyzed by Oxalic Acid Dihydrate

Author(s): Seyed Sajad Sajadikhah* and Bagher Liravi-Deylami

Volume 19, Issue 3, 2022

Published on: 06 May, 2021

Page: [214 - 221] Pages: 8

DOI: 10.2174/1570178618666210506120228

Price: $65

Open Access Journals Promotions 2
Abstract

Benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine, and triazoloquinazolinone derivatives were synthesized via a one-pot multi-component reaction in the presence of a catalytic amount of oxalic acid dihydrate. The reactions were performed in the mixture of EtOH:H2O or under solvent-free conditions as green media. The advantageous features of these methodologies are inexpensive starting materials and catalyst, high atom economy and good yields, and metal-free synthesis. Moreover, all the products were obtained by simple filtration, and no need for column chromatography or tedious separation procedures, which is very important in terms of reducing environmental pollutions.

Keywords: Benzoimidazopyrimidine, benzimidazoloquinazolinone, triazolopyrimidine, triazoloquinazolinone, oxalic acid dehydrate, green chemistry, multi-component reacrion.

Graphical Abstract
[1]
Ahluwalia, V.K.; Varma, R.S. Green Solvent for Organic Synthesis; Alpha Science International: Abingdon, UK, 2009.
[2]
Náray-Szabó, G.; Mika, L.T. Green Chem., 2018, 20, 2171-2191.
[http://dx.doi.org/10.1039/C8GC00514A]
[3]
Boureghda, C.; Khodja, I.A.; Carboni, B.; Boulcina, R.; Kermiche, O.; Debache, A. Lett. Org. Chem., 2016, 13, 482-490.
[http://dx.doi.org/10.2174/1570178613666160822164749]
[4]
Chaudhary, A. Curr. Org. Chem., 2019, 23, 1945-1983.
[http://dx.doi.org/10.2174/1385272823666191019110010]
[5]
Karimi-Jaberi, Z.; Fereydoonnezhad, A. Iran. Chem. Commun., 2017, 5, 407-416.
[6]
Banerjee, B. Curr. Org. Chem., 2018, 22, 208-233.
[http://dx.doi.org/10.2174/1385272821666170703123129]
[7]
Chinchkar, S.M.; Patil, J.D.; Korade, S.N.; Gokavi, G.S.; Shejawal, R.V.; Pore, D.M. Lett. Org. Chem., 2017, 14, 403-408.
[http://dx.doi.org/10.2174/1570178614666170426163442]
[8]
Elwahy, A.H.M.; Shaaban, M.R. RSC Advances, 2015, 5, 75659-75710.
[http://dx.doi.org/10.1039/C5RA11421G]
[9]
Summer, D.; Matuszczak, B. Lett. Org. Chem., 2019, 16, 25-29.
[http://dx.doi.org/10.2174/1570178615666180713091531]
[10]
Youseftabar-Miri, L.; Hosseinjani-Pirdehi, H. Green Chem., 2017, 1, 56-68.
[11]
Hassankhani, A. Chem. Commun. (Camb.), 2019, 1, 248-256.
[12]
Kaur, N.; Kaur, K.; Raj, T.; Kaur, G.; Singh, A.; Aree, T.; Park, S-J.; Kim, T-J.; Singh, N.; Jang, D.O. Tetrahedron, 2015, 71, 332-337.
[http://dx.doi.org/10.1016/j.tet.2014.11.039]
[13]
Chiang, A.N.; Valderramos, J-C.; Balachandran, R.; Chovatiya, R.J.; Mead, B.P.; Schneider, C.; Bell, S.L.; Klein, M.G.; Huryn, D.M.; Chen, X.S.; Day, B.W.; Fidock, D.A.; Wipf, P.; Brodsky, J.L. Bioorg. Med. Chem., 2009, 17(4), 1527-1533.
[http://dx.doi.org/10.1016/j.bmc.2009.01.024] [PMID: 19195901]
[14]
Zanatta, N.; Amaral, S.S.; Esteves-Souza, A.; Echevarria, A.; Brondani, P.B.; Flores, D.C.; Bonacorso, H.G.; Flores, A.F.C.; Martins, M.A.P. Synthesis, 2006, 14, 2305-2312.
[http://dx.doi.org/10.1055/s-2006-942444]
[15]
Chitra, S.; Devanathan, D.; Pandiarajan, K. Eur. J. Med. Chem., 2010, 45(1), 367-371.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.018] [PMID: 19800716]
[16]
Trivedi, A.R.; Bhuva, V.R.; Dholariya, B.H.; Dodiya, D.K.; Kataria, V.B.; Shah, V.H. Bioorg. Med. Chem. Lett., 2010, 20(20), 6100-6102.
[http://dx.doi.org/10.1016/j.bmcl.2010.08.046] [PMID: 20813528]
[17]
Kumar, B.R.P.; Sankar, G.; Baig, R.B.N.; Chandrashekaran, S. Eur. J. Med. Chem., 2009, 44, 4129-4198.
[18]
Renyu, Q.; Yuchao, L.; Kandegama, W.M.W.W.; Qiong, C.; Guangfu, Y. Mini Rev. Med. Chem., 2018, 18(9), 781-793.
[http://dx.doi.org/10.2174/1389557517666171101112850] [PMID: 29090667]
[19]
Ivachtchenko, A.V.; Golovina, E.S.; Kadieva, M.G.; Koryakova, A.G.; Kovalenko, S.M.; Mitkin, O.D.; Okun, I.M.; Ravnyeyko, I.M.; Tkachenko, S.E.; Zaremba, O.V. Bioorg. Med. Chem., 2010, 18(14), 5282-5290.
[http://dx.doi.org/10.1016/j.bmc.2010.05.051] [PMID: 20541425]
[20]
Oukoloff, K.; Lucero, B.; Francisco, K.R.; Brunden, K.R.; Ballatore, C. Eur. J. Med. Chem., 2019, 165, 332-346.
[http://dx.doi.org/10.1016/j.ejmech.2019.01.027] [PMID: 30703745]
[21]
Gol, R.M.; Khatri, T.T.; Barot, V.M. Chem. Heterocycl. Compd., 2019, 55, 246-253.
[http://dx.doi.org/10.1007/s10593-019-02449-x]
[22]
Alagarsamy, V.; Pathak, U.S. Bioorg. Med. Chem., 2007, 15(10), 3457-3462.
[http://dx.doi.org/10.1016/j.bmc.2007.03.007] [PMID: 17391966]
[23]
Alagarsamy, V.; Revathi, R.; Meena, S.; Ramaseshu, K.V.; Rajasekaran, S.; De Clercq, E. Indian J. Pharm. Sci., 2004, 66, 459-462.
[24]
Alagarsamy, V.; Solomon, V.R.; Murugan, M. Bioorg. Med. Chem., 2007, 15(12), 4009-4015.
[http://dx.doi.org/10.1016/j.bmc.2007.04.001] [PMID: 17452107]
[25]
Alagarsamy, V.; Murugananthan, G.; Venkateshperumal, R. Biol. Pharm. Bull., 2003, 26(12), 1711-1714.
[http://dx.doi.org/10.1248/bpb.26.1711] [PMID: 14646176]
[26]
Gujral, M.L.; Saxena, P.N.; Tiwari, R.S. Indian J. Med. Res., 1955, 43(4), 637-641.
[PMID: 13278034]
[27]
Karimi, M.; Naimi-Jamal, M.R. J. Saudi Chem. Soc., 2019, 23, 182-187.
[http://dx.doi.org/10.1016/j.jscs.2018.06.007]
[28]
Glasser, A.C.; Diamond, L.; Combs, G. J. Pharm. Sci., 1971, 60(1), 127-129.
[http://dx.doi.org/10.1002/jps.2600600128] [PMID: 5548222]
[29]
Malamiri, F.; Khaksar, S.; Badri, R.; Tahanpesar, E. Curr. Org. Synth., 2019, 16(8), 1185-1190.
[http://dx.doi.org/10.2174/1570179416666191018145142] [PMID: 31984925]
[30]
Dam, B.; Jamatia, R.; Gupta, A.; Pal, A.K. ACS Sustain. Chem.& Eng., 2017, 5, 11459-11469.
[http://dx.doi.org/10.1021/acssuschemeng.7b02626]
[31]
Raj, T.; Sharma, H. ACS Sustain. Chem.& Eng., 2017, 5, 1468-1475.
[http://dx.doi.org/10.1021/acssuschemeng.6b02030]
[32]
Liu, J.; Lei, M.; Hu, L. Green Chem., 2012, 14, 840-846.
[http://dx.doi.org/10.1039/c2gc16499j]
[33]
Chang-Sheng, Y.; Song, L.; Cui-Hua, W.; Chen-Xia, Y.; Qing-Qing, S.; Shu-Jiang, T. Chin. J. Chem., 2008, 26, 2107-2111.
[http://dx.doi.org/10.1002/cjoc.200890376]
[34]
Mousavi, M.R.; Maghsoodlou, M.T.; Hazeri, N.; Habibi-Khorassani, S.M.J. Iran. Chem. Soc., 2015, 12, 1419-1424.
[http://dx.doi.org/10.1007/s13738-015-0609-9]
[35]
Mousavi, M.R.; Maghsoodlou, M.T. Monatsh. Chem., 2014, 145, 1967-1973.
[http://dx.doi.org/10.1007/s00706-014-1273-y]
[36]
Chen, L-H.; Chung, T-W.; Narhe, B.D.; Sun, C-M. ACS Comb. Sci., 2016, 18(3), 162-169.
[http://dx.doi.org/10.1021/acscombsci.5b00186] [PMID: 26871300]
[37]
Heravi, M.M.; Ranjbar, L.; Derikvand, F.; Alimadadi, B.; Oskooie, H.A.; Bamoharram, F.F. Mol. Divers., 2008, 12(3-4), 181-185.
[http://dx.doi.org/10.1007/s11030-008-9086-8] [PMID: 18780153]
[38]
Puligoundla, R.G.; Karnakanti, S.; Bantu, R.; Kommu, N.; Kondra, S.B.; Nagarapu, L. Tetrahedron Lett., 2013, 54, 2480-2483.
[http://dx.doi.org/10.1016/j.tetlet.2013.02.099]
[39]
Mousavi, M.R.; Maghsoodlou, M.T.J. Iran. Chem. Soc., 2015, 12, 743-749.
[http://dx.doi.org/10.1007/s13738-014-0533-4]
[40]
Adrom, B.; Hazeri, N.; Lashkari, M.; Maghsodlou, M.T. J. Chem. Res., 2016, 40, 458-460.
[http://dx.doi.org/10.3184/174751916X14664307728623]

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