Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Review Article

Sustainable Green Synthesis of Pyrimidine Derivatives: Review on Multicomponent Synthesis, Catalysts and Techniques

Author(s): Elshimaa Mohmed Eid*

Volume 21, Issue 2, 2024

Published on: 08 June, 2023

Page: [127 - 139] Pages: 13

DOI: 10.2174/1570179420666230330081211

Price: $65

Abstract

“The founder of green chemistry explains how chemicals manufacturing must change to support a sustainable future.” In this review, Green chemistry is considered in the synthesis of heterocycles compounds containing Pyrimidine nuclei using different catalyzes, solvents, and techniques for the synthesis of pyrimidine derivatives that achieve sustainability. The mentioned fused heterocycles are classified according to the type of ring system. The yield of the target molecules reported in the review is given in the reaction's last step.

Keywords: Sustainable chemistry, green chemistry, pyrimidine synthesis, green catalysts, microwave techniques, solvent-free reactions, ultrasonic waves.

Next »
Graphical Abstract
[1]
Green chemistry and the future of sustainability-harvard extension school. Available from: https://extension.harvard.edu/blog/green-chemistry-and-the-future-of-sustainability/ (Accessed on: 17 June 2022).
[2]
Cunningham, M.F.; Campbell, J.D.; Fu, Z.; Bohling, J.; Leroux, J.G.; Mabee, W.; Robert, T. Future green chemistry and sustainability needs in polymeric coatings. Green Chem., 2019, 21(18), 4919-4926.
[http://dx.doi.org/10.1039/C9GC02462J]
[3]
Green and Sustainable Chemistry-UNEP - UN Environment Programme. Available from: https://www.unep.org/explore-topics/chemicals-waste/what-we-do/policy-and-governance/green-and-sustainable-chemistry (Accessed on: 17 June 2022).
[4]
Karamthulla, S.; Jana, A.; Choudhury, L.H. Synthesis of novel 5,6-disubstituted pyrrolo [2,3- d]Pyrimidine-2,4-Diones via one-pot three-component reactions. ACS Comb. Sci., 2017, 19(2), 108-112.
[http://dx.doi.org/10.1021/acscombsci.6b00147] [PMID: 28036166]
[5]
Ryzhkova, Y.E.; Fakhrutdinov, A.N.; Elinson, M.N. Green on-water multicomponent approach for the synthesis of pyrrolo[2,3-d]pyrimidines. Tetrahedron Lett., 2021, 81, 153336.
[http://dx.doi.org/10.1016/j.tetlet.2021.153336]
[6]
Bistrović Popov, A.; Vianelo, R.; Grbčić P.; Sedić M.; Pavelić S.K.; Pavelić K.; Raić-Malić S. Novel Bis- and Mono-Pyrrolo[2,3-d]pyrimidine and purine derivatives: Synthesis, computational analysis and antiproliferative evaluation. Molecules, 2021, 26(11), 3334.
[http://dx.doi.org/10.3390/molecules26113334] [PMID: 34206076]
[7]
Shaabani, A.; Seyyedhamzeh, M.; Ganji, N.; Hamidzad Sangachin, M.; Armaghan, M. One-pot four-component synthesis of highly substituted [1,2,4]triazolo[1,5-a]pyrimidines. Mol. Divers., 2015, 19(4), 709-715.
[http://dx.doi.org/10.1007/s11030-015-9604-4] [PMID: 26016722]
[8]
Pismataro, M.C.; Felicetti, T.; Bertagnin, C.; Nizi, M.G.; Bonomini, A.; Barreca, M.L.; Cecchetti, V.; Jochmans, D.; De Jonghe, S.; Neyts, J.; Loregian, A.; Tabarrini, O.; Massari, S. 1,2,4-Triazolo[1,5-a]pyrimidines: Efficient one-step synthesis and functionalization as influenza polymerase PA-PB1 interaction disruptors. Eur. J. Med. Chem., 2021, 221, 113494-113494.
[http://dx.doi.org/10.1016/j.ejmech.2021.113494] [PMID: 33962311]
[9]
Abdallah, M.; Gomha, S.; Abbas, I.; Kazem, M.; Alterary, S.; Mabkhot, Y. An efficient synthesis of novel pyrazole-based heterocycles as potential antitumor agents. Appl. Sci., 2017, 7(8), 785.
[http://dx.doi.org/10.3390/app7080785]
[10]
Bakherad, M.; Bagherian, G.; Rezaeifard, A.; Mosayebi, F.; Shokoohi, B.; Keivanloo, A. Synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines in the magnetized deionized water based on UV–visible study. J. Indian Chem. Soc., 2021, 18(4), 839-852.
[http://dx.doi.org/10.1007/s13738-020-02073-z]
[11]
Bhat, A.R.; Dongre, R.S.; Naikoo, G.A.; Hassan, I.U.; Ara, T. Proficient synthesis of bioactive annulated pyrimidine derivatives: A review. J. Taibah Univ. Sci., 2017, 11(6), 1047-1069.
[http://dx.doi.org/10.1016/j.jtusci.2017.05.005]
[12]
Bhat, A.R.; Shalla, A.H.; Dongre, R.S. Dibutylamine (DBA): A highly efficient catalyst for the synthesis of pyrano[2,3- d]pyrimidine derivatives in aqueous media. J. Taibah Univ. Sci., 2016, 10(1), 9-18.
[http://dx.doi.org/10.1016/j.jtusci.2015.03.004]
[13]
Jain, S.; Paliwal, P.K.; Neelaiah Babu, G.; Bhatewara, A. DABCO promoted one-pot synthesis of dihydropyrano(c)chromene and pyrano[2,3-d]pyrimidine derivatives and their biological activities. J. Saudi Chem. Soc., 2014, 18(5), 535-540.
[http://dx.doi.org/10.1016/j.jscs.2011.10.023]
[14]
Bhat, A.R.; Shalla, A.H.; Dongre, R.S. Synthesis of new annulated pyrano[2,3-d]pyrimidine derivatives using organo catalyst (DABCO) in aqueous media. J. Saudi Chem. Soc., 2017, 21, S305-S310.
[http://dx.doi.org/10.1016/j.jscs.2014.03.008]
[15]
Mokhtari, T.S.; Amrollahi, M.A.; Sheikhhosseini, E.; Sheibani, H.; Nezhad, S.S. Poly(4-vinylpyridine) catalyzed synthesis and characterization of Pyrano[2,3-d]pyrimidine derivatives as potent antibacterial agents. Curr. Bioact. Compd., 2018, 14(1), 54-59.
[http://dx.doi.org/10.2174/1573407213666170104153128]
[16]
Maleki, N.; Shakarami, Z.; Jamshidian, S.; Nazari, M. Clean synthesis of pyrano[2,3- D]pyrimidines using ZnO nano-powders. Acta Chem. Iasi, 2016, 24(1), 20-28.
[http://dx.doi.org/10.1515/achi-2016-0002]
[17]
Ziarani, G.M.; Faramarzi, S.; Asadi, S.; Badiei, A.; Bazl, R.; Amanlou, M. Three-component synthesis of pyrano[2,3-d]-pyrimidine dione derivatives facilitated by sulfonic acid nanoporous silica (SBA-Pr-SO3H) and their docking and urease inhibitory activity. Daru, 2013, 21(1), 3.
[http://dx.doi.org/10.1186/2008-2231-21-3] [PMID: 23351402]
[18]
Mollashahi, E.; Nikraftar, M. Nano-SiO2 catalyzed three-component preparations of pyrano[2,3- d]pyrimidines, 4H-chromenes, and dihydropyrano[3,2- c]chromenes. J. Saudi Chem. Soc., 2018, 22(1), 42-48.
[http://dx.doi.org/10.1016/j.jscs.2017.06.003]
[19]
Wang, X. Zeng, Z.; Shi, D.; Wei, X.; Zong, Z. KF-alumina catalyzed one-pot synthesis of Pyrido[2,3-d]Pyrimidine Derivatives. Synth. Commun., 2004, 34(23), 4331-4338.
[http://dx.doi.org/10.1081/SCC-200039392]
[20]
Saglam, D.; Turgut, Z.; Saglam, D.; Turgut, Z. One-Pot Synthesis of Pyrido[2,3-d]pyrimidines Catalyzed by Bismuth(III). Triflate. Int. J. Org. Chem., 2022, 12(1), 11-27.
[http://dx.doi.org/10.4236/ijoc.2022.121002]
[21]
Samai, S.; Chandra Nandi, G.; Chowdhury, S.; Singh, M.S. l-Proline catalyzed synthesis of densely functionalized pyrido[2,3-d]pyrimidines via three-component one-pot domino Knoevenagel aza-Diels–Alder reaction. Tetrahedron, 2011, 67(33), 5935-5941.
[http://dx.doi.org/10.1016/j.tet.2011.06.051]
[22]
Rad, A.M.; Mokhtary, M. Efficient one-pot synthesis of pyrido[2,3-d]pyrimidines catalyzed by nanocrystalline MgO in water. Int. Nano Lett., 2015, 5(2), 109-123.
[http://dx.doi.org/10.1007/s40089-015-0145-8]
[23]
Farahmand, T.; Hashemian, S.; Sheibani, A. Efficient one-pot synthesis of pyrano[2,3-d]pyrimidinone and pyrido [2,3-d] pyrimidine derivatives by using of Mn-ZIF-8@ZnTiO3 nanocatalyst. J. Mol. Struct., 2020, 1206, 127667.
[http://dx.doi.org/10.1016/j.molstruc.2019.127667]
[24]
Parrey, I.R.; Hashmi, A.A. Retraction: One-pot synthesis of new Pyrido [2,3-d] Pyrimidine derivatives under ultrasonic irradiation using organo catalyst 4-Dimethylaminopyridine (DMAP). Catal. Sustain. Energy, 2017, 4(1), 7.
[http://dx.doi.org/10.1515/cse-2017-0002]
[25]
Naeimi, H.; Didar, A.; Rashid, Z.; Zahraie, Z. Sonochemical synthesis of pyrido[2,3-d:6,5-d’]-dipyrimidines catalyzed by [HNMP]+[HSO4]- and their antimicrobial activity studies. J. Antibiot., 2017, 70, 845-852.
[http://dx.doi.org/10.1038/ja.2017.47] [PMID: 28442734]
[26]
Nia, R.H.; Mamaghani, M.; Tabatabaeian, K.; Shirini, F.; Rassa, M. A rapid one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives using Brّnsted-acidic ionic liquid as catalyst. Acta Chim. Slov., 2013, 60(4), 889-895.
[PMID: 24362994]
[27]
Abdolmohammadi, S.; Afsharpour, M. Facile one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives over ZrO2 nanoparticles catalyst. Chin. Chem. Lett., 2012, 23(3), 257-260.
[http://dx.doi.org/10.1016/j.cclet.2012.01.001]
[28]
Mohsenimehr, M.; Mamaghani, M.; Shirini, F.; Sheykhan, M.; Moghaddam, F.A. One-pot synthesis of novel pyrido[2,3-d]pyrimidines using HAp-encapsulated-γ-Fe2O3 supported sulfonic acid nanocatalyst under solvent-free conditions. Chin. Chem. Lett., 2014, 25(10), 1387-1391.
[http://dx.doi.org/10.1016/j.cclet.2014.04.025]
[29]
Rangel, J. Díaz-Uribe, C.; Rodriguez-Serrano, A.; Zarate, X.; Serge, Y.; Vallejo, W.; Nogueras, M.; Trilleras, J.; Quiroga, J.; Tatchen, J.; Cobo, J. Three-component one-pot synthesis of novel pyrido[2,3-d]pyrimidine indole substituted derivatives and DFT analysis. J. Mol. Struct., 2017, 1137, 431-439.
[http://dx.doi.org/10.1016/j.molstruc.2017.02.038]
[30]
Khalafy, J.; Rimaz, M.; Rabiei, H.; Panahi, L. An efficient one-pot protocol for regioselective synthesis of 3-aryl-6,8-dialkyl-7-thioxo-7,8-dihydropyrimido[4,5-c] pyridazine-5(6 H)-ones. J. Sulfur Chem., 2013, 34(4), 395-406.
[http://dx.doi.org/10.1080/17415993.2012.745126]
[31]
Shinde, S.V.; Jadhav, W.N.; Karade, N.N. Three component solvent-free synthesis and fungicidal activity of substituted pyrimido [4,5-d] pyrimidine-2-(1h)-one. Orient. J. Chem., 2010, 26(1), 307-317.
[32]
Majumder, S.; Borah, P.; Bhuyan, P.J. An efficient and regioselective one-pot multi-component synthesis of pyrimido[4,5-d]pyrimidine derivatives in water. Tetrahedron Lett., 2014, 55(6), 1168-1170.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.095]
[33]
Mohebat, R.; Mosslemin, M.H.; Dehghan-Darehshiri, A.; Hassanabadi, A. Three-component reaction between 6-amino- N, - dimethyluracil and ammonium thiocyanate in the presence of aroyl chlorides under solvent-free conditions. J. Sulfur Chem., 2011, 32(6), 557-561.
[http://dx.doi.org/10.1080/17415993.2011.619537]
[34]
Heravi, M.; Daraie, M. A novel and efficient five-component synthesis of pyrazole based Pyrido[2,3-d]pyrimidine-diones in water: A triply green synthesis. Molecules, 2016, 21(4), 441.
[http://dx.doi.org/10.3390/molecules21040441] [PMID: 27043522]
[35]
Satasia, S.P.; Kalaria, P.N.; Raval, D.K. Catalytic regioselective synthesis of pyrazole based pyrido[2,3-d]pyrimidine-diones and their biological evaluation. Org. Biomol. Chem., 2014, 12(11), 1751-1758.
[http://dx.doi.org/10.1039/c3ob42132e] [PMID: 24496121]
[36]
Chebanov, V.; Muravyova, E.; Shishkina, S.; Musatov, V.; Knyazeva, I.; Shishkin, O.; Desenko, S. Chemoselectivity of multicomponent condensations of barbituric acids, 5-Aminopyrazoles, and aldehydes. Synthesis, 2009, 2009(8), 1375-1385.
[http://dx.doi.org/10.1055/s-0028-1088024]
[37]
Kudale, A.A.; Kendall, J.; Miller, D.O.; Collins, J.L.; Bodwell, G.J. Povarov reactions involving 3-aminocoumarins: Synthesis of 1,2,3,4-Tetrahydropyrido[2,3- c]coumarins and Pyrido[2,3-c]coumarins. J. Org. Chem., 2008, 73(21), 8437-8447.
[http://dx.doi.org/10.1021/jo801411p] [PMID: 18821803]
[38]
Jiang, B.; Rajale, T.; Wever, W.; Tu, S.J.; Li, G. Multicomponent reactions for the synthesis of heterocycles. Chem. Asian J., 2010, 5(11), 2318-2335.
[http://dx.doi.org/10.1002/asia.201000310] [PMID: 20922748]
[39]
Shaker, R.M.; Ishak, E.A. Barbituric acid utility in multi-component reactions. Z. Naturforsch. B. J. Chem. Sci., 2011, 66(12), 1189-1201.
[http://dx.doi.org/10.1515/znb-2011-1201]
[40]
Azizian, J.; Mohammadi, A.A.; Karimi, A.R.; Mohammadizadeh, M.R. KAl(SO4)2·12H2O supported on silica gel as a novel heterogeneous system catalyzed biginelli reaction. Appl. Catal. A Gen., 2006, 300(1), 85-88.
[http://dx.doi.org/10.1016/j.apcata.2005.11.001]
[41]
Velpula, R.; Banothu, J.; Gali, R.; Deshineni, R.; Bavantula, R. 1-Sulfopyridinium chloride: Green and expeditious ionic liquid for the one-pot synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent-free conditions. Chin. Chem. Lett., 2015, 26(3), 309-312.
[http://dx.doi.org/10.1016/j.cclet.2014.11.030]
[42]
Mohammadi, B.; Behbahani, F.K. Recent developments in the synthesis and applications of dihydropyrimidin-2(1H)-ones and thiones. Mol. Divers., 2018, 22(2), 405-446.
[http://dx.doi.org/10.1007/s11030-017-9806-z] [PMID: 29349521]
[43]
Khalafi-Nezhad, A.; Sarikhani, S.; Shahidzadeh, E.S.; Panahi, F. l-Proline-promoted three-component reaction of anilines, aldehydes and barbituric acids/malononitrile: regioselective synthesis of 5-arylpyrimido[4,5-b]quinoline-diones and 2-amino-4-arylquinoline-3-carbonitriles in water. Green Chem., 2012, 14(10), 2876-2884.
[http://dx.doi.org/10.1039/c2gc35765h]
[44]
Bhat, A.R.; Dongre, R.S. One-pot synthesis of annulated pyrido[2,3-d:6,5-d]dipyrimidine derivatives using nitrogen based DBU catalyst in aqueous ethanol medium. J. Taiwan Inst. Chem. Eng., 2015, 56, 191-195.
[http://dx.doi.org/10.1016/j.jtice.2015.04.020]
[45]
Abdolmohammadi, S.; Balalaie, S.; Barari, M.; Rominger, F. Three-component green reaction of arylaldehydes, 6-amino-1,3- dimethyluracil and active methylene compounds catalyzed by Zr(HSO4)4 under solvent-free conditions. Comb. Chem. High Throughput Screen., 2013, 16(2), 150-159.
[http://dx.doi.org/10.2174/1386207311316020009] [PMID: 23092170]
[46]
Mosslemin, M.H.; Nateghi, M.R. Rapid and efficient synthesis of fused heterocyclic pyrimidines under ultrasonic irradiation. Ultrason. Sonochem., 2010, 17(1), 162-167.
[http://dx.doi.org/10.1016/j.ultsonch.2009.07.002] [PMID: 19679502]
[47]
Naeimi, H.; Didar, A.; Rashid, Z.; Zahraie, Z. Sonochemical synthesis of pyrido[2,3-d:6,5-d']-dipyrimidines catalyzed by [HNMP]+[HSO4]- and their antimicrobial activity studies. J. Antibiot., 2017, 70(7), 845-852.
[http://dx.doi.org/10.1038/ja.2017.47] [PMID: 28442734]
[48]
Mohammadi Ziarani, G.; Badiei, A.; Aslani, Z.; Lashgari, N. Application of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) in the green one-pot synthesis of triazoloquinazolinones and benzimidazoquinazolinones. Arab. J. Chem., 2015, 8(1), 54-61.
[http://dx.doi.org/10.1016/j.arabjc.2011.06.020]
[49]
Goli-Jolodar, O.; Shirini, F. An efficient and practical synthesis of benzazolo[2,1-b]quinazolinones and triazolo[2,1-b]quinazolinones catalyzed by nano-sized NS-C4(DABCO-SO3H)2)·4Cl. J. Indian Chem. Soc., 2017, 14(11), 2275-2286.
[http://dx.doi.org/10.1007/s13738-017-1164-3]
[50]
Tu, S.J.; Zhang, Y.; Jiang, H.; Jiang, B.; Zhang, J.Y.; Jia, R.H.; Shi, F. A Simple Synthesis of Furo[3'4'5,6]pyrido[2,3-d]pyrimidine Derivatives through Multicomponent Reactions in Water. Eur. J. Org. Chem., 2007, 2007(9), 1522-1528.
[http://dx.doi.org/10.1002/ejoc.200600913]
[51]
Mamaghani, M.; Shirini, F.; Bassereh, E.; Hossein Nia, R. 1,2-Dimethyl- N -butanesulfonic acid imidazolium hydrogen sulfate as efficient ionic liquid catalyst in the synthesis of indeno fused pyrido[2,3- d]pyrimidines. J. Saudi Chem. Soc., 2016, 20(5), 570-576.
[http://dx.doi.org/10.1016/j.jscs.2014.12.003]
[52]
Tu, S.; Cao, L.; Zhang, Y.; Shao, Q.; Zhou, D.; Li, C. An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives and related compounds under ultrasound irradiation without catalyst. Ultrason. Sonochem., 2008, 15(3), 217-221.
[http://dx.doi.org/10.1016/j.ultsonch.2007.03.002] [PMID: 17466564]
[53]
Ia, R. A multi-component reaction to 6-aminothiouracils: Synthesis, mechanistic study and antitumor activity. Chemotherapy, 2016, 5(3), 212.
[http://dx.doi.org/10.4172/2167-7700.1000212]

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