Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Green and Regioselective Alkylation of Dihydropyrimidinthiones through Michael Addition

Author(s): Fatemeh Yaghoubi, Gholamhassan Imanzadeh*, Roghayyeh Asgharzadeh, Zahra Soltanzadeh and Turan Öztürk

Volume 20, Issue 12, 2023

Published on: 04 August, 2023

Page: [1159 - 1169] Pages: 11

DOI: 10.2174/1570178620666230622115431

Price: $65

Abstract

Dihydropyrimidines are one of the most important heterocyclic ring systems having a serious place in medicinal and organic synthesis. In this paper, a new series of dihydropyrimidines consisting of sulfur atoms were synthesized using inorganic base K2CO3 and TBAB as an organic salt to make high polarity in reaction media. Interestingly, different 3,4-dihydropyrimidin-2(1H)-thiones reacted smoothly with various acrylic esters to afford adducts via highly regioselective N3-Michael addition reaction was carried out at 100oC in 12 h. result: Unfortunately, the reaction failed with fumaric esters owing steric effects. Avoiding organic solvents during this reaction effectively led to the development of an economic approach. Structures of the new compounds were established on the basis of 1H NMR, 13C NMR, and IR spectral data.

« Previous Next »
Graphical Abstract

[1]
Kirk-Othmer Clark, E. Encyclopedia of Chemical Technology; Wiley.: New York, 1997, 23, pp. 134-146.
[2]
Page, P.C.B., Ed. Organo-sulfur Chemistry I and II; Springer: Berlin, 1999.
[3]
Zhao, N.; Li, Y.; Wang, Y.; Wang, J. J. Sulfur Chem., 2006, 27(5), 427-432.
[http://dx.doi.org/10.1080/17415990600863752]
[4]
Francioso, A.; Baseggio Conrado, A.; Mosca, L.; Fontana, M. Oxid. Med. Cell. Longev., 2020, 2020, 1-27.
[http://dx.doi.org/10.1155/2020/8294158]
[5]
Karelson, M.M.; Katritzky, A.R.; Szafran, M.; Zerner, M.C. J. Org. Chem., 1989, 54(26), 6030-6034.
[http://dx.doi.org/10.1021/jo00287a012]
[6]
Soni, R.; Singh, G.; Kaur, R.; Kaur, G.; Gill, R.K. Bariwal. J. Chem. Biol., 2014, 4, 163-175.
[7]
Kaur, R.; Chaudhary, S.; Kumar, K.; Gupta, M.K.; Rawal, R.K. Eur. J. Med. Chem., 2017, 132, 108-134.
[http://dx.doi.org/10.1016/j.ejmech.2017.03.025] [PMID: 28342939]
[8]
Aslam, M.; Verma, S. Int. J. Chemtech Res., 2012, 4, 109-111.
[9]
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]
[10]
Biginelli, P. Gazz. Chim. Ital., 1893, 23, 360-413.
[11]
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]
[12]
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.; O’Malley, S.S.; Olah, T.V.; Ellis, J.D.; Barrish, A.; Kassahun, K.; Leppert, P.; Nagarathnam, D.; Forray, C. J. Med. Chem., 2000, 43(14), 2703-2718.
[http://dx.doi.org/10.1021/jm990612y] [PMID: 10893308]
[13]
Klein, E.; DeBonis, S.; Thiede, B.; Skoufias, D.A.; Kozielski, F.; Lebeau, L. Bioorg. Med. Chem., 2007, 15(19), 6474-6488.
[http://dx.doi.org/10.1016/j.bmc.2007.06.016] [PMID: 17587586]
[14]
Zabihollahi, R.; Vahabpour, R.; Hartoonian, C.; Sedaghati, B.; Sadat, S.M.; Soleymani, M.; Ranjbar, M.; Fassihi, A.; Aghasadeghi, M.R. Acta Virol., 2012, 56, 11-18.
[http://dx.doi.org/10.4149/av_2012_01_11] [PMID: 22404604]
[15]
Bahekar, S.S.; Shinde, D.B. Bioorg. Med. Chem. Lett., 2004, 14(7), 1733-1736.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.039] [PMID: 15026060]
[16]
Sedaghati, B.; Fassihi, A.; Arbabi, S.; Ranjbar, M.; Memarian, H.R.; Saghaie, L.; Omidi, A.; Sardari, A.; Jalali, M.; Abedi, D. Med. Chem. Res., 2012, 21(12), 3973-3983.
[http://dx.doi.org/10.1007/s00044-011-9931-7]
[17]
Aladdin, M.S.; Abd El-Hamid, A.I.; Salah, M.E.; Ibrahim, F.Z. Z. Naturforsch. C, 2009, 64c, 483-489.
[18]
Kamaljit, S.; Kawaljit, S.; Baojie, W.; Scott, F.; Kelly, C.; Jan, B. Eur. J. Med. Chem., 2011, 46, 2290-2294.
[http://dx.doi.org/10.1016/j.ejmech.2011.03.010] [PMID: 21450375]
[19]
Atwal, K.S.; Swanson, B.N.; Unger, S.E.; Floyd, D.M.; Moreland, S.; Hedberg, A.; Reilly, O. J. Med. Chem., 1991, 34, 806-811.
[http://dx.doi.org/10.1021/jm00106a048] [PMID: 1995904]
[20]
Salem, M.A.I.; Marzouk, M.I.; Salem, M.S.; Alshibani, G.A. J. Heterocycl. Chem., 2016, 53(2), 545-557.
[http://dx.doi.org/10.1002/jhet.2358]
[21]
Shaabani, A.; Bazgir, A.; Teimouri, F. Tetrahedron Lett., 2003, 44(4), 857-859.
[http://dx.doi.org/10.1016/S0040-4039(02)02612-6]
[22]
Gartner, M.; Sunder-Plassmann, N.; Seiler, J.; Utz, M.; Vernos, I.; Surrey, T.; Giannis, A. ChemBioChem, 2005, 6(7), 1173-1177.
[http://dx.doi.org/10.1002/cbic.200500005] [PMID: 15912555]
[23]
Haggarty, S.J.; Mayer, T.U.; Miyamoto, D.T.; Fathi, R.; King, R.W.; Mitchison, T.J.; Schreiber, S.L. Chem. Biol., 2000, 7(4), 275-286.
[http://dx.doi.org/10.1016/S1074-5521(00)00101-0] [PMID: 10780927]
[24]
Mayer, T.U.; Kapoor, T.M.; Haggarty, S.J.; King, R.W.; Schreiber, S.L.; Mitchison, T. J. Sci., 1999, 286(5441), 971-974.
[http://dx.doi.org/10.1126/science.286.5441.971] [PMID: 10542155]
[25]
Kappe, C.O.; Shishkin, O.V.; Uray, G.; Verdino, P. Tetrahedron, 2000, 56(13), 1859-1862.
[http://dx.doi.org/10.1016/S0040-4020(00)00116-2]
[26]
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]
[27]
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]
[28]
Mansouri, M.; Movahedian, A.; Rostami, M.; Fassihi, A. Res. Pharm. Sci., 2012, 7(4), 257-264.
[PMID: 23248677]
[29]
Dömling, A.; Wang, W.; Wang, K. Chem. Rev., 2012, 112(6), 3083-3135.
[http://dx.doi.org/10.1021/cr100233r] [PMID: 22435608]
[30]
Rotstein, B.H.; Zaretsky, S.; Rai, V.; Yudin, A.K. Chem. Rev., 2014, 114(16), 8323-8359.
[http://dx.doi.org/10.1021/cr400615v] [PMID: 25032909]
[31]
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]
[32]
Piqani, B.; Zhang, W. Beilstein J. Org. Chem., 2011, 7, 1294-1298.
[http://dx.doi.org/10.3762/bjoc.7.150] [PMID: 21977214]
[33]
Salem, M.A.I.; Madkour, H.M.F.; Marzouk, M.I.; Azab, M.E.; Mahmoud, N.F.H. Phosphorus Sulfur Silicon Relat. Elem., 2008, 183(10), 2596-2614.
[http://dx.doi.org/10.1080/10426500801967963]
[34]
Singh, K.; Singh, S. Tetrahedron, 2008, 64(51), 11718-11723.
[http://dx.doi.org/10.1016/j.tet.2008.10.001]
[35]
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]
[36]
Singh, K.; Singh, S. Tetrahedron Lett., 2006, 47(46), 8143-8146.
[http://dx.doi.org/10.1016/j.tetlet.2006.09.039]
[37]
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]
[38]
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]
[39]
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]
[40]
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]
[41]
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]
[42]
Andrews, B.; Ahmed, M. Asian J. Chem., 2013, 25(4), 2070-2072.
[http://dx.doi.org/10.14233/ajchem.2013.13320]
[43]
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]
[44]
Kappe, C.O. Acc. Chem. Res., 2000, 33(12), 879-888.
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
[45]
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]
[46]
Ahmed, E.A.; Soliman, A.M.M.; Ali, A.M.; Ali El-Remaily, M.A.E.A.A. Appl. Organomet. Chem., 2021, 35(5), 6197-6205.
[http://dx.doi.org/10.1002/aoc.6197]
[47]
Ali El-Remaily, M.A.E.A.A.; Hamad, H.A.; Soliman, A.M.M.; Elhady, O.M. Appl. Organomet. Chem., 2021, 35(7), 6238-6248.
[http://dx.doi.org/10.1002/aoc.6238]
[48]
Ali El-Remaily, M.A.; Elhady, O.M. chemistryselect., 2020, 5, 12098-12101.
[49]
Bonabi, S.; Imanzadeh, G.H.; Asgharzadeh, R. Soltanzadeh. Z. Lett. Org. Chem., 2022, 19, 1118-1127.
[http://dx.doi.org/10.2174/1570178619666220509094205]
[50]
Imanzadeh, G.; Aliabadi, A.; Zamanloo, M. Green Chem. Lett. Rev., 2016, 9(2), 106-113.
[http://dx.doi.org/10.1080/17518253.2016.1177606]
[51]
Imanzadeh, G.; Rezaee-Gatar, S. ARKIVOC, 2015, 2015(5), 121-133.
[http://dx.doi.org/10.3998/ark.5550190.p009.048]
[52]
Imanzadeh, G.; Banaei, A.; Fathi, T.; Soltanzadeh, Z. Green Chem. Lett. Rev., 2017, 10(1), 1-9.
[http://dx.doi.org/10.1080/17518253.2016.1250958]
[53]
Zare, Z.; Imanzadeh, G. Soltanzadeh. Z. Lett. Org. Chem., 2017, 14(5), 347-352.
[http://dx.doi.org/10.2174/1570178614666170321125529]
[54]
Atabak, S.; Imanzadeh, G.; Asgharzadeh, R.; Soltanzadeh, Z.; Öztürk, T. J. Sulfur Chem., 2023, 0, 1-15.
[http://dx.doi.org/10.1080/17415993.2023.2173010]
[55]
Imanzadeh, G.; Rezaei, H.; Asgharzadeh, R.; Soltanzadeh, Z. J. Sulfur Chem., 2021, 42(4), 359-368.
[http://dx.doi.org/10.1080/17415993.2021.1890738]
[56]
Soltanzadeh, Z. Imanzadeh, G.; Noroozi-Pesyan, N.; Şahin, E.; Hooshmand, H. Tetrahedron, 2016, 72(14), 1736-1741.
[http://dx.doi.org/10.1016/j.tet.2016.02.024]
[57]
Imanzadeh, G.; Zolfagharzadeh, S. Soltanzadeh. Z. Lett. Org. Chem., 2021, 18(2), 107-114.
[http://dx.doi.org/10.2174/1570178617999200818170632]
[58]
Imanzadeh, G.; Asgharzadeh, R. Soltanzadeh. Z. Lett. Org. Chem., 2022, 19(11), 1005-1012.
[http://dx.doi.org/10.2174/1570178619666220127123822]
[59]
Soltanzadeh, Z. Imanzadeh, G.; Noroozi-Pesyan, N.; Şahin. E. Green Chem. Lett. Rev., 2017, 10(2), 107-116.
[http://dx.doi.org/10.1080/17518253.2017.1307459]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy