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Letters in Organic Chemistry

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Research Article

K2CO3/TBAB, a Composite of Inorganic and Organic Salts, a Novel and Powerful Media for Regioselective Michael Addition of Dihydropyrimidinones to Acrylic Esters Under and Without Solvent Conditions

Author(s): Sevil Bonabi, Gholamhassan Imanzadeh*, Roghayyeh Asgharzadeh and Zahra Soltanzadeh

Volume 19, Issue 12, 2022

Published on: 11 August, 2022

Page: [1118 - 1127] Pages: 10

DOI: 10.2174/1570178619666220509094205

Price: $65

Abstract

Aims: Synthesis of dihydropyrimidinones derivatives.

Background: carrying out reactions in the green route and organic solvent-free conditions.

Objective: Regioselective Michael addition of dihydropyrimidinones to acrylic esters.

Methods: The reaction proceeded in the presence of K2CO3/TBAB, a media of inorganic base K2CO3 and organic ionic salt TBAB (tetrabutylammonium bromide) at 100°C.

Results: A series of new dihydropyrimidinone derivatives using aza-Michael addition reaction were synthesized under solvent-free conditions.

Conclusion: The reaction is characterized by high efficiency, relatively short reaction time, high yields, simple environmentally friendly reaction conditions.

Other: The reaction of acrylic esters with dihydropyrimidinones produced N3-substituted derivative of dihydropyrimidinones with 85-95% yields in 6 h.

Keywords: Regioselective synthesis, dihydropyrimidinones, aza-Michael addition, acrylic esters, solvent conditions, organic salts.

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[1]
Biginelli, P. Gazz. Chim. Ital., 1893, 23, 360-413.
[2]
Kappe, C.O. Eur. J. Med. Chem., 2000, 35(12), 1043-1052.
[http://dx.doi.org/10.1016/S0223-5234(00)01189-2] [PMID: 11248403]
[3]
Kappe, C.O.; Stadler, A. Org. React., 2004, 63, 1-116.
[4]
Nasr-Esfahani, M.; Montazerozohori, M.; Aghel-mirrezaee, M.; Kashi, H. J. Chil. Chem. Soc., 2014, 59(1), 2311-2314.
[http://dx.doi.org/10.4067/S0717-97072014000100015]
[5]
Kappe, C.O. Tetrahedron, 1993, 49, 6937-6963.
[http://dx.doi.org/10.1016/S0040-4020(01)87971-0]
[6]
Atwal, K.S.; Rovnyak, G.C.; Kimball, S.D.; Floyd, D.M.; Moreland, S.; Swanson, B.N.; Gougoutas, J.Z.; Schwartz, J.; Smillie, K.M.; Malley, M.F. J. Med. Chem., 1990, 33(9), 2629-2635.
[http://dx.doi.org/10.1021/jm00171a044] [PMID: 2391701]
[7]
Nagarathanm, D.; Miao, S.W.; Lagu, B.; Chiu, G.; Fang, J.; Dhar, T.G.M.; Zhang, J.; Tyagarajan, S.; Marzabadi, M.R.; Zhang, F.Q.; Wong, W.C.; Sun, W.Y.; Tian, D.; Wetzel, J.M.; Forray, C.; Chang, R.S.L.; Broten, T.P.; Ransom, R.W.; Schorn, T.W.; Chen, T.B.; O’Malley, S.; Kling, P.; Schneck, K.; Bendesky, R.; Harrell, C.M.; Vyas, K.P.; Gluchowski, C. J. Med. Chem., 1999, 42, 4764-4777.
[http://dx.doi.org/10.1021/jm990200p] [PMID: 10579840]
[8]
Mayer, T.U.; Kapoor, T.M.; Haggarty, S.J.; King, R.W.; Schreiber, S.L.; Mitchison, T.J. Science, 1999, 286(5441), 971-974.
[http://dx.doi.org/10.1126/science.286.5441.971] [PMID: 10542155]
[9]
Bruce, M.A.; Pointdexter, G.S.; Johnson, G. WO9833,791. PCT Int. Appl. Chem. Abstr., 1998, 129, 148989g.
[10]
Goldmann, S.; Stoltefuß, J.; Paessens, A.; Graef, E.; Lottmann, S.D.E. 19,817,262. Ger. Offen. Chem. Abstr., 1999, 131, 286535y.
[11]
Wichmann, J.; Adam, G.; Kolczewski, S.; Mutel, V.; Woltering, T. Bioorg. Med. Chem. Lett., 1999, 9(11), 1573-1576.
[http://dx.doi.org/10.1016/S0960-894X(99)00227-9] [PMID: 10386938]
[12]
Atwal, K.S.; Swanson, B.N.; Unger, S.E.; Floyd, D.M.; Moreland, S.; Hedberg, A.; O’Reilly, B.C. J. Med. Chem., 1991, 34(2), 806-811.
[http://dx.doi.org/10.1021/jm00106a048] [PMID: 1995904]
[13]
Rovnyak, G.C.; Atwal, K.S.; Hedberg, A.; Kimball, S.D.; Moreland, S.; Gougoutas, J.Z.; O’Reilly, B.C.; Schwartz, J.; Malley, M.F. J. Med. Chem., 1992, 35(17), 3254-3263.
[http://dx.doi.org/10.1021/jm00095a023] [PMID: 1387168]
[14]
Grover, G.J.; Dzwonczyk, S.; McMullen, D.M.; Normandin, D.E.; Parham, C.S.; Sleph, P.G.; Moreland, S. J. Cardiovasc. Pharmacol., 1995, 26(2), 289-294.
[http://dx.doi.org/10.1097/00005344-199508000-00015] [PMID: 7475054]
[15]
Rovnyak, G.C.; Kimball, S.D.; Beyer, B.; Cucinotta, G.; DiMarco, J.D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J.P.; Zhang, R.; Moreland, S. J. Med. Chem., 1995, 38(1), 119-129.
[http://dx.doi.org/10.1021/jm00001a017] [PMID: 7837222]
[16]
Schnell, B.; Strauss, U.T.; Verdino, P.; Faber, K.; Kappe, C.O. Tetrahedron Asymmetry, 2000, 11(7), 1449-1453.
[http://dx.doi.org/10.1016/S0957-4166(00)00081-1]
[17]
Fabian, W.M.F.; Semones, M.A.; Kappe, C.O. J. Mol. Struct. THEOCHEM, 1998, 432(3), 219-228.
[http://dx.doi.org/10.1016/S0166-1280(98)00061-X]
[18]
Fatima, A.; Braga, T.C.; Neto, L.S.; Terra, B.S.; Oliveira, B.G.F.; Silva, D.L.; Modolo, L.V. J. Adv. Res., 2015, 6, 363-373.
[http://dx.doi.org/10.1016/j.jare.2014.10.006] [PMID: 26257934]
[19]
Aron, Z.D.; Overman, L.E. J. Am. Chem. Soc., 2005, 127(10), 3380-3390.
[http://dx.doi.org/10.1021/ja042875+] [PMID: 15755156]
[20]
Arnold, M.A.; Day, K.A.; Durón, S.G.; Gin, D.Y. J. Am. Chem. Soc., 2006, 128(40), 13255-13260.
[http://dx.doi.org/10.1021/ja063860+] [PMID: 17017806]
[21]
Makarieva, T.N.; Tabakmaher, K.M.; Guzii, A.G.; Denisenko, V.A.; Dmitrenok, P.S.; Shubina, L.K.; Kuzmich, A.S.; Lee, H.S.; Stonik, V.A. J. Nat. Prod., 2011, 74(9), 1952-1958.
[http://dx.doi.org/10.1021/np200452m] [PMID: 21848268]
[22]
Lewis, R.W.; Mabry, J.; Polisar, J.G.; Eagen, K.P.; Ganem, B.; Hess, G.P. Biochemistry, 2010, 49(23), 4841-4851.
[http://dx.doi.org/10.1021/bi100119t]
[23]
Zhu, X.; Zhao, G.; Zhou, X.; Xu, X.; Xia, G.; Zheng, Z.; Wang, L.; Yang, X.; Li, S. Bioorg. Med. Chem. Lett., 2010, 20(1), 299-301.
[http://dx.doi.org/10.1016/j.bmcl.2009.10.119] [PMID: 19897363]
[24]
Dhumaskar, K.L.; Meena, S.N.; Ghadi, S.C.; Tilve, S.G. Bioorg. Med. Chem. Lett., 2014, 24(13), 2897-2899.
[http://dx.doi.org/10.1016/j.bmcl.2014.04.099] [PMID: 24835627]
[25]
Treptow, T.G.M.; Figueiró, F.; Jandrey, E.H.; Battastini, A.M.O.; Salbego, C.G.; Hoppe, J.B.; Taborda, P.S.; Rosa, S.B.; Piovesan, L.A.; Montes D’Oca, C.R.; Russowsky, D.; Montes D’Oca, M.G. Eur. J. Med. Chem., 2015, 95, 552-562.
[http://dx.doi.org/10.1016/j.ejmech.2015.03.062] [PMID: 25863023]
[26]
Chikhale, R.; Menghani, S.; Babu, R.; Bansode, R.; Bhargavi, G.; Karodia, N.; Rajasekharan, M.V.; Paradkar, A.; Khedekar, P. Eur. J. Med. Chem., 2015, 96, 30-46.
[http://dx.doi.org/10.1016/j.ejmech.2015.04.011] [PMID: 25874329]
[27]
Rashid, U.; Sultana, R.; Shaheen, N.; Hassan, S.F.; Yaqoob, F.; Ahmad, M.J.; Iftikhar, F.; Sultana, N.; Asghar, S.; Yasinzai, M.; Ansari, F.L.; Qureshi, N.A. Eur. J. Med. Chem., 2016, 115, 230-244.
[http://dx.doi.org/10.1016/j.ejmech.2016.03.022] [PMID: 27017551]
[28]
Singh, K.; Kaur, T. MedChemComm, 2016, 7(5), 739-748.
[http://dx.doi.org/10.1039/C6MD90025A]
[29]
Singh, K.; Arora, D.; Singh, K.; Singh, S. Mini Rev. Med. Chem., 2009, 9(1), 95-106.
[http://dx.doi.org/10.2174/138955709787001686] [PMID: 19149663]
[30]
Singh, T.P.; Singh, O.M. Nova Science Publishers: New York, 2012, p. 117-135.
[31]
Kim, S.S.; Choi, B.S.; Lee, J.H.; Lee, K.K.; Lee, T.H.; Kim, Y.H.; Hyunik, S. Synlett, 2009, 4, 599-602.
[32]
Yamamoto, K.; Chen, Y.G.; Buono, F.G. Org. Lett., 2005, 7(21), 4673-4676.
[http://dx.doi.org/10.1021/ol051879w] [PMID: 16209507]
[33]
Wang, X.C.; Quan, Z.J.; Zhang, Z. Tetrahedron, 2007, 63(34), 8227-8233.
[http://dx.doi.org/10.1016/j.tet.2007.05.108]
[34]
Pérez, R.; Beryozkina, T.; Zbruyev, O.I.; Haas, W.; Kappe, C.O. J. Comb. Chem., 2002, 4(5), 501-510.
[http://dx.doi.org/10.1021/cc0200181] [PMID: 12217023]
[35]
Lengar, A.; Kappe, C.O. Org. Lett., 2004, 6(5), 771-774.
[http://dx.doi.org/10.1021/ol036496h] [PMID: 14986971]
[36]
Chikhale, R.V.; Bhole, R.P.; Khedekar, P.B.; Bhusari, K.P. Eur. J. Med. Chem., 2009, 44(9), 3645-3653.
[http://dx.doi.org/10.1016/j.ejmech.2009.02.021] [PMID: 19321237]
[37]
Barrow, J.C.; Nantermet, P.G.; Selnick, H.G.; Glass, K.L.; Rittle, K.E.; Gilbert, K.F.; Steele, T.G.; Homnick, C.F.; Freidinger, R.M.; Ransom, R.W.; Kling, P.; Reiss, D.; Broten, T.P.; Schorn, T.W.; Chang, R.S.L. J. Med. Chem., 2000, 43, 2703-2718.
[http://dx.doi.org/10.1021/jm990612y] [PMID: 10893308]
[38]
Terracciano, S.; Lauro, G.; Strocchia, M.; Fischer, K.; Werz, O.; Riccio, R.; Bruno, I.; Bifulco, G. ACS Med. Chem. Lett., 2015, 6(2), 187-191.
[http://dx.doi.org/10.1021/ml500433j] [PMID: 25699159]
[39]
Crespo, A.; El Maatougui, A.; Biagini, P.; Azuaje, J.; Coelho, A.; Brea, J.; Loza, M.I.; Cadavid, M.I.; García-Mera, X.; Gutiérrez-de-Terán, H.; Sotelo, E. ACS Med. Chem. Lett., 2013, 4(11), 1031-1036.
[http://dx.doi.org/10.1021/ml400185v] [PMID: 24900602]
[40]
Maatougui, A.E.; Azuaje, J.; Gonzalez-Gomez, M.; Miguez, G.; Crespo, A.; Carbajales, C.; Escalante, L.; Garcia-Mera, X.; Teran, H.G.; Sotelo, E. J. Med. Chem., 2016, 59, 1967-1983.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01586] [PMID: 26824742]
[41]
Singh, K.; Singh, S. Tetrahedron, 2008, 64(51), 11718-11723.
[http://dx.doi.org/10.1016/j.tet.2008.10.001]
[42]
Kassaee, M.Z.; Masrouri, H.; Movahedi, F.; Mohammadi, R. Helv. Chim. Acta, 2010, 93(2), 261-264.
[http://dx.doi.org/10.1002/hlca.200900197]
[43]
Singh, K.; Singh, S. Tetrahedron Lett., 2006, 47(46), 8143-8146.
[http://dx.doi.org/10.1016/j.tetlet.2006.09.039]
[44]
Quan, Z.J.; Xu, Q.; Zhang, Z.; Da, Y.X.; Wang, X.C. Tetrahedron, 2013, 69(2), 881-887.
[http://dx.doi.org/10.1016/j.tet.2012.10.097]
[45]
Shen, Y.; Liu, Q.; Wu, G.; Wu, L. Tetrahedron Lett., 2008, 49(7), 1220-1222.
[http://dx.doi.org/10.1016/j.tetlet.2007.12.035]
[46]
Putatunda, S.; Chakraborty, S.; Ghosh, S.; Nandi, P.; Chakraborty, S.; Sen, P.C.; Chakraborty, A. Eur. J. Med. Chem., 2012, 54, 223-231.
[http://dx.doi.org/10.1016/j.ejmech.2012.04.043] [PMID: 22658336]
[47]
Singh, K.; Arora, D.; Poremsky, E.; Lowery, J.; Moreland, R.S. Eur. J. Med. Chem., 2009, 44(5), 1997-2001.
[http://dx.doi.org/10.1016/j.ejmech.2008.10.002] [PMID: 19008020]
[48]
Akhaja, T.N.; Raval, J.P. Eur. J. Med. Chem., 2011, 46(11), 5573-5579.
[http://dx.doi.org/10.1016/j.ejmech.2011.09.023] [PMID: 21981980]
[49]
Andrews, B.; Ahmed, M. Asian J. Chem., 2013, 25(4), 2070-2070.
[http://dx.doi.org/10.14233/ajchem.2013.13320]
[50]
Heravi, M.M.; Asadi, S.; Lashkariani, B.M. Mol. Divers., 2013, 17(2), 389-407.
[http://dx.doi.org/10.1007/s11030-013-9439-9] [PMID: 23588897]
[51]
Kappe, C.O. Acc. Chem. Res., 2000, 33(12), 879-888.
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
[52]
Zhu, C.; Yang, B.; Zhao, Y.; Fu, C.; Tao, L.; Wei, Y. Polym. Chem., 2013, 4(21), 5395-5400.
[http://dx.doi.org/10.1039/c3py00553d]
[53]
Patil, S.R.; Choudhary, A.S.; Patil, V.S.; Sekar, N. Fibers Polym., 2015, 16(11), 2349-2358.
[http://dx.doi.org/10.1007/s12221-015-5233-x]
[54]
Boukis, A.C.; Llevot, A.; Meier, M.A.R. Macromol. Rapid Commun., 2016, 37(7), 643-649.
[http://dx.doi.org/10.1002/marc.201500717] [PMID: 26800511]
[55]
Zhao, Y.; Yu, Y.; Zhang, Y.; Wang, X.; Yang, B.; Zhang, Y.; Zhang, Q.; Fu, C.; Weia, Y.; Tao, L. Polym. Chem., 2015, 6(27), 4940-4945.
[http://dx.doi.org/10.1039/C5PY00684H]
[56]
Imanzadeh, G.H.; Banaei, A.; Fathi, T.; Soltanzadeh, Z. Green Chem. Lett. Rev., 2016, 10(1), 1-9.
[http://dx.doi.org/10.1080/17518253.2016.1250958]
[57]
Soltanzadeh, Z.; Imanzadeh, G.H.; Noroozi-Pesyan, N.; Şahin, E.; Hooshmand, H. Tetrahedron, 2016, 72(14), 1736-1741.
[http://dx.doi.org/10.1016/j.tet.2016.02.024]
[58]
Imanzadeh, G.H.; Zolfagharzadeh, S.; Soltanzadeh, Z. Lett. Org. Chem., 2021, 18, 107-114.
[http://dx.doi.org/10.2174/1570178617999200818170632]
[59]
Safari, N.; Imanzadeh, G.H.; Asgharzadeh, R.; Hosseyni, S.T.; Shamkhali, A.N.; Soltanzadeh, Z. Chem. Heterocycl. Compd., 2021, 57(6), 640-645.
[http://dx.doi.org/10.1007/s10593-021-02962-y]
[60]
Imanzadeh, G.H.; Soltanizadeh, Z.; Khodayari, A.; Zamanloo, M.; Mansoori, Y.; Salehzadeh, J. Chin. J. Chem., 2012, 30(4), 891-899.
[http://dx.doi.org/10.1002/cjoc.201100351]
[61]
Asgharzadeh, R.; Imanzadeh, G.H.; Soltanzadeh, Z. Green Chem. Lett. Rev., 2017, 10(2), 80-87.
[http://dx.doi.org/10.1080/17518253.2017.1293177]
[62]
Tian, H.; Yang, H.; Tian, C.; An, G.; Li, G. Org. Lett., 2020, 22(19), 7709-7715.
[http://dx.doi.org/10.1021/acs.orglett.0c02912] [PMID: 32942860]
[63]
Cheng, Y.; Yu, S.; He, Y.; An, G.; Li, G.; Yang, Z. Chem. Sci. (Camb.), 2021, 12(9), 3216-3225.
[http://dx.doi.org/10.1039/D0SC05409G]
[64]
Nagarajaiah, H.; Mukhopadhyay, A.; Moorthy, J.N. Tetrahedron Lett., 2016, 57(47), 5135-5149.
[http://dx.doi.org/10.1016/j.tetlet.2016.09.047]
[65]
Oboudatian, H.S.; Naeimi, H.; Moradian, M. RSC Advances, 2021, 11(13), 7271-7279.
[http://dx.doi.org/10.1039/D0RA09929E]
[66]
Yao, B.J.; Wu, W.X.; Ding, L.G.; Dong, Y.B. J. Org. Chem., 2021, 86(3), 3024-3032.
[http://dx.doi.org/10.1021/acs.joc.0c02423] [PMID: 33416316]
[67]
Zhao, Z.; Dai, H.; Shi, L. Chem. Pap., 2021, 75(2), 583-590.
[http://dx.doi.org/10.1007/s11696-020-01327-7]

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