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Letters in Organic Chemistry

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

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Research Article

Highly Efficient Synthesis of Imidazolecarboxylate Salts via Sequential Nucleophilic Addition-Intramolecular Cyclization Reactions

Author(s): Maryam Nazarahari and Javad Azizian*

Volume 20, Issue 1, 2023

Published on: 12 September, 2022

Page: [54 - 60] Pages: 7

DOI: 10.2174/1570178619666220819152744

Price: $65

Abstract

In this work, we used a highly efficient and easy approach for synthesizing imidazolecarboxylate salt through the reaction between α-amidino carboxylic acids and α-halo ketones with as readily available starting materials in the presence of KHCO3 at THF under reflux. Targeted synthesis of this type of imidazole bearing the carboxylic acid group in a single structure, in addition to the biological properties enriched as a ligand, is very popular in the manufacture of catalysts. The salient features of this protocol include eco-friendly, high atom-economical, easy and mild conditions that led to the production of all products with high yields. Furthermore, all products were purified without the need for column chromatography through the GAP chemistry (group-assisted purification chemistry) technique.

Keywords: Imidazole, amino acid, intramolecular cyclization, GAP chemistry, eprosartan, etomidate.

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[1]
(a) Shalini, K.; Sharma, P.K.; Kumar, N. Chem. Sin., 2010, 1, 36-47.;
(b) Shaabani, A.; Nazeri, M.T.; Afshari, R. Mol. Divers., 2019, 23(3), 751-807.
[http://dx.doi.org/10.1007/s11030-018-9902-8] [PMID: 30552550];
(c) Nazeri, M.T.; Shaabani, A.; Notash, B. Org. Biomol. Chem., 2021, 19(16), 3722-3734.
[http://dx.doi.org/10.1039/D0OB02339F] [PMID: 33908431]
[2]
Vázquez-Salazar, A.; Becerra, A.; Lazcano, A. PLoS One, 2018, 13(4), e0196349.
[http://dx.doi.org/10.1371/journal.pone.0196349] [PMID: 29698445]
[3]
Sawaya, A.C.H.F.; Vaz, B.G.; Eberlin, M.N.; Mazzafera, P. Genet. Resour. Crop Evol., 2011, 58(3), 471-480.
[http://dx.doi.org/10.1007/s10722-011-9660-2]
[4]
Stark, H.; Kathmann, M.; Schlicker, E.; Schunack, W.; Schlegel, B.; Sippl, W. Mini Rev. Med. Chem., 2004, 4(9), 965-977.
[http://dx.doi.org/10.2174/1389557043403107] [PMID: 15544557]
[5]
Santos, A.P.; Moreno, P.R.H. Natural Products; Ramawat, K.; Mérillon, J.M., Eds.; Springer-Verlag: Berlin, Heidelberg, 2013, pp. 861-882.
[http://dx.doi.org/10.1007/978-3-642-22144-6_27]
[6]
Kameshima, W.; Ishizuka, T.; Minoshima, M.; Yamamoto, M.; Sugiyama, H.; Xu, Y.; Komiyama, M. Angew. Chem. Int. Ed., 2013, 52(51), 13681-13684.
[http://dx.doi.org/10.1002/anie.201305489]
[7]
(a) Luca, L.D. Curr. Med. Chem., 2006, 13, 1-23.
[PMID: 16457636];
(b) Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron, 2007, 63(22), 4571-4624.
[http://dx.doi.org/10.1016/j.tet.2007.02.075]
[8]
(a) Foye, W.O. Foye's principles of medicinal chemistry, 6th Ed.; Lippincott Williams & Wilkins: Walnut Street, 2008. ;
(b) Nath, S.P. A Text Book of Medicinal Chemistry; SG Publisher, 2004.
[9]
Sennequier, N.; Wolan, D.; Stuehr, D.J. J. Biol. Chem., 1999, 274(2), 930-938.
[http://dx.doi.org/10.1074/jbc.274.2.930] [PMID: 9873034]
[10]
Brimblecombe, R.; Duncan, W.; Durant, G.; Emmett, J.; Ganellin, C.; Parsons, M. J. Int. Med. Res., 1975, 3(2), 86-92.
[http://dx.doi.org/10.1177/030006057500300205]
[11]
Di Santo, R.; Tafi, A.; Costi, R.; Botta, M.; Artico, M.; Corelli, F.; Forte, M.; Caporuscio, F.; Angiolella, L.; Palamara, A.T. J. Med. Chem., 2005, 48(16), 5140-5153.
[http://dx.doi.org/10.1021/jm048997u] [PMID: 16078834]
[12]
(a) Mano, T.; Okumura, Y.; Sakakibara, M.; Okumura, T.; Tamura, T.; Miyamoto, K.; Stevens, R.W. J. Med. Chem., 2004, 47(3), 720-725.
[http://dx.doi.org/10.1021/jm0303554] [PMID: 14736252];
(b) Acharya, P.T.; Bhavsar, Z.A.; Jethava, D.J.; Patel, D.B.; Patel, H.D.A. J. Mol. Struct., 2021, 1226, 129268.
[http://dx.doi.org/10.1016/j.molstruc.2020.129268];
(c) Pandya, K.M.; Patel, J.J.; Patel, A.H.; Patel, N.B.; Desai, P. Lett. Org. Chem., 2021, 18(7), 574-582.
[http://dx.doi.org/10.2174/1570178617999200819164729]
[13]
Coura, J.R.; De Castro, S.L. Mem. Inst. Oswaldo Cruz, 2002, 97(1), 3-24.
[http://dx.doi.org/10.1590/S0074-02762002000100001] [PMID: 11992141]
[14]
(a) Robins, G.W.; Scott, L.J. Drugs, 2005, 65(16), 2355-2377.
[http://dx.doi.org/10.2165/00003495-200565160-00012] [PMID: 16266204];
(b) Jones-Gotman, M.; Sziklas, V.; Djordjevic, J.; Dubeau, F.; Gotman, J.; Angle, M.; Tampieri, D.; Olivier, A.; Andermann, F. Neurology, 2005, 65(11), 1723-1729.
[http://dx.doi.org/10.1212/01.wnl.0000187975.78433.cb] [PMID: 16344513];
(c) Darwish, M.; Burke, J.M.; Hellriegel, E.; Robertson, P., Jr; Phillips, L.; Ludwig, E.; Munteanu, M.C.; Bond, M. Cancer Chemother. Pharmacol., 2014, 73(6), 1119-1127.
[http://dx.doi.org/10.1007/s00280-014-2445-5] [PMID: 24677018]
[15]
(a) Voutchkova, A.M.; Feliz, M.; Clot, E.; Eisenstein, O.; Crabtree, R.H. J. Am. Chem. Soc., 2007, 129(42), 12834-12846.
[http://dx.doi.org/10.1021/ja0742885] [PMID: 17900114];
(b) Sunab, Y-X.; Sun, W-Y. CrystEngComm, 2015, 17, 4045-4063.
[http://dx.doi.org/10.1039/C5CE00372E];
(c) Karami, B.; Eskandari, K.; Azizi, M. Lett. Org. Chem., 2013, 10(10), 722-732.
[http://dx.doi.org/10.2174/15701786113109990044]
[16]
Panda, T.; Kundu, T.; Banerjee, R. Chem. Commun. (Camb.), 2012, 48(44), 5464-5466.
[http://dx.doi.org/10.1039/c2cc31527k] [PMID: 22538292]
[17]
(a) Chen, S-S.; Liu, Q.; Zhao, Y.; Qiao, R.; Sheng, L-Q.; Liu, Z-D.; Yang, S.; Song, C-F. Cryst. Growth Des., 2014, 14(8), 3727-3741.
[http://dx.doi.org/10.1021/cg401811c];
(b) Nazeri, M.T.; Shaabani, A. New J. Chem., 2021, 45(47), 21967-22011.
[http://dx.doi.org/10.1039/D1NJ04514H]
[18]
(a) Gao, W-Y.; Yan, W.; Cai, R.; Meng, L.; Salas, A.; Wang, X-S.; Wojtas, L.; Shi, X.; Ma, S. Inorg. Chem., 2012, 51(8), 4423-4425.
[http://dx.doi.org/10.1021/ic3002256] [PMID: 22449128];
(b) Shaabani, A.; Shadi, M.; Mohammadian, R.; Javanbakht, S.; Nazeri, M.T.; Bahri, F. Appl. Org. Chem., 2019, 33, e5074.;
(c) Feng, D-D.; Zhao, Y-D.; Wang, X-Q.; Fang, D-D.; Tang, J.; Fan, L-M.; Yang, J. Dalton Trans., 2019, 48(29), 10892-10900.
[http://dx.doi.org/10.1039/C9DT01430F] [PMID: 31111141];
(d) Gupta, S.; Pathak, A.K.; Ameta, C.; Punjabi, P.B. Lett. Org. Chem., 2021, 18(4), 318-333.
[http://dx.doi.org/10.2174/1570178617999200708161330]
[19]
Chen, X.D.; Zhao, X.H.; Chen, M.; Du, M. Chemistry, 2009, 15(47), 12974-12977.
[http://dx.doi.org/10.1002/chem.200902306] [PMID: 19902440]
[20]
Helal, C.J.; Lucas, J.C. Org. Lett., 2002, 4(23), 4133-4134.
[http://dx.doi.org/10.1021/ol026892k] [PMID: 12423104]
[21]
Kanazawa, C.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc., 2006, 128(33), 10662-10663.
[http://dx.doi.org/10.1021/ja0617439] [PMID: 16910644]
[22]
Cao, H.; Bie, F-S.; Liu, X-J.; Han, Y.; Ma, J.; Shi, Y-J.; Yan, P.; Sun, C-Y.; Wang, H-M. Tetrahedron, 2020, 76(22), 131205.
[http://dx.doi.org/10.1016/j.tet.2020.131205]
[23]
(a) An, G.; Seifert, C.; Li, G. Org. Biomol. Chem., 2015, 13(6), 1600-1617.
[http://dx.doi.org/10.1039/C4OB02254H] [PMID: 25523061];
(b) Xie, J-B.; Luo, J.; Winn, T.R.; Cordes, D.B.; Li, G. Beilstein J. Org. Chem., 2014, 10, 746-751.
[http://dx.doi.org/10.3762/bjoc.10.69] [PMID: 24778728];
(c) Fan, W.; Chen, K-Y.; Chen, Q-P.; Li, G.; Jiang, B. Org. Biomol. Chem., 2017, 15(31), 6493-6499.
[http://dx.doi.org/10.1039/C7OB01515A] [PMID: 28745373];
(d) Zhang, H.; Yang, Z.; Zhao, B.N.; Li, G. J. Org. Chem., 2018, 83(2), 644-655.
[http://dx.doi.org/10.1021/acs.joc.7b02556] [PMID: 29235341];
(e) Chennapuram, M.; Emmadi, N.R.; Bingi, C.; Nanubolu, J.B.; Atmakur, K. Green Chem., 2014, 16(6), 3237-3246.
[http://dx.doi.org/10.1039/c4gc00388h];
(f) Wang, H.; Liu, X.; Feng, X.; Huang, Z.; Shi, D. Green Chem., 2013, 15(12), 3307-3311.
[http://dx.doi.org/10.1039/c3gc41799a];
(g) Rouh, H.; Tang, Y.; Zhang, S.; Ali, A.I.M.; Unruh, D.; Surowiec, K.; Li, G. Org. Biomol. Chem., 2021, 19(47), 10319-10325.
[http://dx.doi.org/10.1039/D1OB02078A] [PMID: 34812831]
[24]
(a) Nazeri, M.T.; Javanbakht, S.; Shaabani, A.; Khavasi, H.R. ChemistrySelect, 2019, 4(48), 14271-14275.
[http://dx.doi.org/10.1002/slct.201904172];
(b) Nazeri, M.T.; Farhid, H.; Javanbakht, S.; Shaabani, A.; Notash, B. Synlett, 2020, 31, 965-971.
[http://dx.doi.org/10.1055/s-0039-1690887];
(c) Rouh, H.; Tang, Y.; Zhang, S.; Ali, A.I.M.; Surowiec, K.; Unruh, D.; Li, G. RSC Advances, 2021, 11(63), 39790-39796.
[http://dx.doi.org/10.1039/D1RA08323F] [PMID: 35494146];
(d) Alizadeh, A.; Rezaiyehraad, R. Chem. Heterocycl. Compd., 2021, 57(3), 239-244.
[http://dx.doi.org/10.1007/s10593-021-02899-2];
(e) Dommaraju, Y.; Prajapati, D. Mol. Divers., 2015, 19, 173-187.;
(f) Fan, W.; Li, Y.-R.; Li, Q.; Jiang, B.; Li, G. Tetrahedron, 2016, 72, 4867-4877.;
(g) Zheng, Y.-X.; Xun, Z.; Zhang, J.-J.; Huang, Z.-B.; Shi, D.-Q. Mol. Divers., 2017, 21, 293-304.;
(h) Patel, D.M.; Vala, R.M.; Sharma, M.G.; Rajani, D.P.; Patel, H.M. ChemistrySelect, 2019, 4, 1031-1041.
[25]
(a) Karimi, A.R.; Alimohammadi, Z.; Azizian, J.; Mohammadi, A.A.; Mohammadizadeh, M. Catal. Commun., 2006, 7(9), 728-732.
[http://dx.doi.org/10.1016/j.catcom.2006.04.004];
(b) Zaghari, Z.; Azizian, J. J. Inorg. Organomet. Polym. Mater., 2019, 29(4), 1076-1083.
[http://dx.doi.org/10.1007/s10904-018-0996-3];
(c) Azimi, S.B.; Azizian, J. Synlett, 2016, 27, 1836-1839.
[http://dx.doi.org/10.1055/s-0035-1561611];
(d) Azizian, J.; Torabi, P.; Noei, J. Tetrahedron Lett., 2016, 57(2), 185-188.
[http://dx.doi.org/10.1016/j.tetlet.2015.11.092];
(e) Ahmadi, S.; Azizian, J. J. Chem. Sci., 2021, 133(4), 1-8.
[http://dx.doi.org/10.1007/s12039-021-01974-7]
[26]
Zaghari, Z.; Azizian, J. Comb. Chem. High Throughput Screen., 2018, 21(8), 609-614.
[http://dx.doi.org/10.2174/1386207321666181114110039] [PMID: 30426895]

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