An Ultrasound-Assisted Solvent and Catalyst-Free Synthesis of Structurally Diverse Pyrazole Centered 1,5-disubstituted Tetrazoles via One-Pot Four-Component Reaction

Page: [795 - 802] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

1,5-Disubstituted tetrazoles are vital drug-like scaffolds usually encountered as valuable bioisosteres of the cis-amide bond. In this article, we reported the synthesis of some novel medicinally relevant pyrazole centered 1,5-disubstituted tetrazoles using ultrasound irradiation via a one-pot 4-C reaction from various pyrazole originated aldehyde, amine, isocyanide, and sodium azide. All the synthesized derivatives were characterized by IR, 1H NMR, 13C NMR, spectroscopic techniques, and mass analysis. This ultrasound-assisted green protocol has several advantages like mild reaction condition, high yield, catalyst and solvent-free reaction protocol, 15 minutes reaction time and easy workup.

Keywords: Ultrasound irradiation, 1, 5-disubstituted tetrazole, pyrazole, catalyst-free, solvent-free, multi-component reaction, green protocol.

Graphical Abstract

[1]
(a) Prabhu, G.; Narendra, N.; Vishwanatha, T.M.; Sureshbabu, V.V. Tetrahedron, 2015, 71(19), 2785-2832.
[http://dx.doi.org/10.1016/j.tet.2015.03.026]
(b) Vagner, J.; Qu, H.; Hruby, V.J. Curr. Opin. Chem. Biol., 2008, 12(3), 292-296.
[http://dx.doi.org/10.1016/j.cbpa.2008.03.009] [PMID: 18423417]
(c) Patch, J.A.; Barron, A.E. Curr. Opin. Chem. Biol., 2002, 6(6), 872-877.
[http://dx.doi.org/10.1016/S1367-5931(02)00385-X] [PMID: 12470744]
(d) Ravichandiran, P.; Subramaniyan, S.A.; Kim, S.Y.; Kim, J.S.; Park, B.H.; Shim, K.S.; Yoo, D.J. ChemMedChem, 2019, 14(5), 532-544.
[http://dx.doi.org/10.1002/cmdc.201800749] [PMID: 30600915]
[2]
(a) Van der Poorten, O.; Knuhtsen, A.; Sejer Pedersen, D.; Ballet, S.; Tourwé, D. J. Med. Chem., 2016, 59(24), 10865-10890.
[http://dx.doi.org/10.1021/acs.jmedchem.6b01029] [PMID: 27690430]
(b) Blaskovich, M.A. J. Med. Chem., 2016, 59(24), 10807-10836.
[http://dx.doi.org/10.1021/acs.jmedchem.6b00319] [PMID: 27589349]
(c) de Graaff, C.; Ruijter, E.; Orru, R.V. Chem. Soc. Rev., 2012, 41(10), 3969-4009.
[http://dx.doi.org/10.1039/c2cs15361k] [PMID: 22546840]
(d) Ko, E.; Liu, J.; Burgess, K. Chem. Soc. Rev., 2011, 40(8), 4411-4421.
[http://dx.doi.org/10.1039/c0cs00218f] [PMID: 21483946]
(e) Ravichandiran, P.; Lai, B.; Gu, Y. Chem. Rec., 2017, 17(2), 142-183.
[http://dx.doi.org/10.1002/tcr.201600042] [PMID: 27492258]
[3]
(a) Ugi, I. Angew. Chem. Int. Ed. Engl., 1962, 1(1), 8-14.
[http://dx.doi.org/10.1002/anie.196200081]
(b) Roh, J.; Vávrová, K.; Hrabálek, A. Eur. J. Org. Chem., 2012, 2012(31), 6101-6118.
[http://dx.doi.org/10.1002/ejoc.201200469]
(c) Yu, K.L.; Johnson, R.L. J. Org. Chem., 1987, 52(10), 2051-2059.
[http://dx.doi.org/10.1021/jo00386a029]
(d) Patil, P.; Khoury, K.; Herdtweck, E.; Dömling, A. Bioorg. Med. Chem., 2015, 23(11), 2699-2715.
[http://dx.doi.org/10.1016/j.bmc.2014.12.021] [PMID: 25630499]
[4]
(a) Sarvary, A.; Maleki, A. Mol. Divers., 2015, 19(1), 189-212.
[http://dx.doi.org/10.1007/s11030-014-9553-3] [PMID: 25273563]
(b) Qian, A.; Zheng, Y.; Wang, R.; Wei, J.; Cui, Y.; Cao, X.; Yang, Y. Bioorg. Med. Chem. Lett., 2018, 28(3), 344-350.
[http://dx.doi.org/10.1016/j.bmcl.2017.12.040] [PMID: 29289430]
[5]
Elavarasan, T.; Sivakumar, D.; Gopalakrishnan, M. J. Pharm. Res., 2018, 12, 749-757.
[6]
(a) Lamie, P.F.; Philoppes, J.N.; Azouz, A.A.; Safwat, N.M. J. Enzyme Inhib. Med. Chem., 2017, 32(1), 805-820.
[http://dx.doi.org/10.1080/14756366.2017.1326110] [PMID: 28587532]
(b) Ravichandiran, P.; Sheet, S.; Premnath, D.; Kim, A.R.; Yoo, D.J. Molecules, 2019, 24(7), 1437.
[http://dx.doi.org/10.3390/molecules24071437] [PMID: 30979056]
(c) Ravichandiran, P. Masłyk, M.; Sheet, S.; Janeczko, M.; Premnath, D.; Kim, A.R.; Park, B.H.; Han, M.K.; Yoo, D.J. ChemistryOpen, 2019, 8(5), 589-600.
[http://dx.doi.org/10.1002/open.201900077] [PMID: 31098338]
[7]
Tukulula, M.; Sharma, R.K.; Meurillon, M.; Mahajan, A.; Naran, K.; Warner, D.; Huang, J.; Mekonnen, B.; Chibale, K. ACS Med. Chem. Lett., 2012, 4(1), 128-131.
[http://dx.doi.org/10.1021/ml300362a] [PMID: 24900574]
[8]
Gao, C.; Chang, L.; Xu, Z.; Yan, X.F.; Ding, C.; Zhao, F.; Wu, X.; Feng, L.S. Eur. J. Med. Chem., 2019, 163, 404-412.
[http://dx.doi.org/10.1016/j.ejmech.2018.12.001] [PMID: 30530192]
[9]
Ponnuvel, K.; Padmini, V.; Sribalan, R. Sens. Actuators B Chem., 2016, 222, 605-611.
[http://dx.doi.org/10.1016/j.snb.2015.08.096]
[10]
Mustafa, S.; Rao, B.U.; Surendrababu, M.S.; Raju, K.K.; Rao, G.N. Chem. Biodivers., 2015, 12(10), 1516-1534.
[http://dx.doi.org/10.1002/cbdv.201400369] [PMID: 26460557]
[11]
Doyle, A.G.; Jacobsen, E.N. Chem. Rev., 2007, 107(12), 5713-5743.
[http://dx.doi.org/10.1021/cr068373r] [PMID: 18072808]
[12]
(a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem. Int. Ed., 2004, 43(15), 1983-1986.
[http://dx.doi.org/10.1002/anie.200352724] [PMID: 15065280]
(b) Gao, H.; Shreeve, J.M. Chem. Rev., 2011, 111(11), 7377-7436.
[http://dx.doi.org/10.1021/cr200039c] [PMID: 21838230]
[13]
Aromí, G.; Barrios, L.A.; Roubeau, O.; Gamez, P. Coord. Chem. Rev., 2011, 255(5-6), 485-546.
[http://dx.doi.org/10.1016/j.ccr.2010.10.038]
[14]
Gutmann, B.; Roduit, J.P.; Roberge, D.; Kappe, C.O. Angew. Chem. Int. Ed. Engl., 2010, 49(39), 7101-7105.
[http://dx.doi.org/10.1002/anie.201003733] [PMID: 20718066]
[15]
Clémençon, I.F.; Ganem, B. Tetrahedron, 2007, 63(35), 8665-8669.
[http://dx.doi.org/10.1016/j.tet.2007.03.127]
[16]
Chakraborty, R.R.; Ghosh, P. Tetrahedron Lett., 2018, 59(40), 3616-3619.
[http://dx.doi.org/10.1016/j.tetlet.2018.08.050]
[17]
Neochoritis, C.G.; Zhao, T.; Dömling, A. Chem. Rev., 2019, 119(3), 1970-2042.
[http://dx.doi.org/10.1021/acs.chemrev.8b00564] [PMID: 30707567]
[18]
Hajra, S.; Sinha, D.; Bhowmick, M. J. Org. Chem., 2007, 72(5), 1852-1855.
[http://dx.doi.org/10.1021/jo062432j] [PMID: 17266377]
[19]
Patil, P.; Zhang, J.; Kurpiewska, K. Kalinowska-Tłuścik, J.; Dömling, A. Synthesis, 2016, 48(8), 1122-1130.
[http://dx.doi.org/10.1055/s-0035-1561353]
[20]
Safa, K.D.; Shokri, T.; Abbasi, H. Teimuri-Mofrad, R. J. Heterocycl. Chem., 2014, 51(1), 80-84.
[http://dx.doi.org/10.1002/jhet.1858]
[21]
Wang, Y.; Patil, P.; Kurpiewska, K.; Kalinowska-Tluscik, J.; Dömling, A. ACS Comb. Sci., 2017, 19(3), 193-198.
[http://dx.doi.org/10.1021/acscombsci.7b00009] [PMID: 28181791]
[22]
Pharande, S.G.; Escobosa, A.R.C.; Gámez-Montaño, R. Green Chem., 2017, 19(5), 1259-1262.
[http://dx.doi.org/10.1039/C6GC03324E]
[23]
Cano, P.A.; Islas-Jácome, A.; Rangel-Serrano, Á.; Anaya-Velázquez, F.; Padilla-Vaca, F.; Trujillo-Esquivel, E.; Ponce-Noyola, P.; Martínez-Richa, A.; Gámez-Montaño, R. Molecules, 2015, 20(7), 12436-12449.
[http://dx.doi.org/10.3390/molecules200712436] [PMID: 26184131]
[24]
Shahrisa, A.; Esmati, S. Synlett, 2013, 24(5), 595-602.
[http://dx.doi.org/10.1055/s-0032-1318221]
[25]
Bekhit, A.A.; Ashour, H.M.; Abdel Ghany, Y.S.; Bekhit, A-D.; Baraka, A. Eur. J. Med. Chem., 2008, 43(3), 456-463.
[http://dx.doi.org/10.1016/j.ejmech.2007.03.030] [PMID: 17532544]
[26]
Damljanović, I.; Vukićević, M.; Radulović, N.; Palić, R.; Ellmerer, E.; Ratković, Z.; Joksović, M.D.; Vukićević, R.D. Bioorg. Med. Chem. Lett., 2009, 19(4), 1093-1096.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.006] [PMID: 19167220]
[27]
Chovatia, P.T.; Akabari, J.D.; Kachhadia, P.K.; Zalavadia, P.D.; Joshi, H.S. J. Serb. Chem. Soc., 2006, 71(7), 713-720.
[http://dx.doi.org/10.2298/JSC0607713C]
[28]
Cui, Y.J.; Tang, L.Q.; Zhang, C.M.; Liu, Z.P. Molecules, 2019, 24(2), 279.
[http://dx.doi.org/10.3390/molecules24020279] [PMID: 30642134]
[29]
Hassan, S.Y. Molecules, 2013, 18(3), 2683-2711.
[http://dx.doi.org/10.3390/molecules18032683] [PMID: 23449067]
[30]
Swami, S.; Devi, N.; Agarwala, A.; Singh, V.; Shrivastava, R. Tetrahedron Lett., 2016, 57(12), 1346-1350.
[http://dx.doi.org/10.1016/j.tetlet.2016.02.045]
[31]
Swami, S.; Agarwala, A.; Shrivastava, R. Mol. Divers., 2017, 21(1), 81-88.
[http://dx.doi.org/10.1007/s11030-016-9699-2] [PMID: 27670881]
[32]
Kazemizadeh, A.R.; Hajaliakbari, N.; Hajian, R.; Shajari, N.; Ramazani, A. Helv. Chim. Acta, 2012, 95(4), 594-597.
[http://dx.doi.org/10.1002/hlca.201100327]
[33]
Hegarty, A.F.; Tynan, N.M.; Fergus, S. J. Chem. Soc. Perkin Trans., 2002, 2(7), 1328-1334.
[http://dx.doi.org/10.1039/b202005j]