Abstract
A variety of dihydropyrimidone compounds were synthesised using an effective one-pot, multicomponent, environmentally friendly reaction of aromatic aldehydes, urea/thiourea, ethyl acetoacetate, and glycerol/ethyl lactate. To the best of our knowledge, this is the first catalyst-free strategy for the synthesis of this key scaffold with medicinal chemistry applications. Other significant aspects of the current approach consist of the employment of glycerol/ethyl lactate as a biodegradable and environmentally friendly reaction medium-cum-promoter, the use of easily available substrates, moderate reaction conditions, ease of use, a wide substrate scope, a short reaction time, easy workup, and excellent yields, and atom efficiency, which make the disclosed procedure an excellent alternative to existing methods.
Graphical Abstract
(b) Horváth, IT; Anastas, P.T. Chem. Rev.-Columbus, 2007, 107(6), 2169-2173.
[http://dx.doi.org/10.1039/C8GC01276H]
[http://dx.doi.org/10.1016/j.apsusc.2023.157530];
(b) Zheng, J.; Zang, S.; Hu, C.; Nie, L.; Chen, H.; Chu, X.; Wang, H.; Ma, M.; Lai, Q. J. Power Sources, 2023, 559, 232634.
[http://dx.doi.org/10.1016/j.jpowsour.2023.232634];
(c) Lane, M. K. M.; Rudel, H. E.; Wilson, J. A.; Erythropel, H. C.; Backhaus, A.; Gilcher, E. B.; Ishii, M.; Jean, C. F.; Lin, F.; Muellers, T. D.; Wang, T. Nature Sus., 2023, 1-11.;
(d) Zang, S.; Hu, C.; Lai, Q.; Nie, L.; Chen, H.; Yi, R.; Ma, M.; Zheng, J. ACS Appl. Mater. Interfaces, 2022, 14(39), 44479-44487.
[http://dx.doi.org/10.1021/acsami.2c13533] [PMID: 36129817];
(e) Zheng, J.; Nie, L.; Hu, C.; Zang, S.; Pang, Y.; Chen, N.; Ma, M.; Lai, Q. ACS Appl. Mater. Interfaces, 2022, 14(49), 54698-54707.
[http://dx.doi.org/10.1021/acsami.2c15574] [PMID: 36472417]
[http://dx.doi.org/10.1039/C1CS15041C] [PMID: 21562677]
[http://dx.doi.org/10.1021/cr050989d] [PMID: 17535020]
[http://dx.doi.org/10.1039/C5GC00611B]
[http://dx.doi.org/10.1002/chem.201705577] [PMID: 29178195];
(b) Santoro, S.; Ferlin, F.; Luciani, L.; Ackermann, L.; Vaccaro, L. Green Chem., 2017, 19(7), 1601-1612.
[http://dx.doi.org/10.1039/C7GC00067G]
[http://dx.doi.org/10.1021/acs.chemrev.7b00571] [PMID: 29300087];
(b) Sheldon, R. A. Green biocatalysis, 2016, 1-15.;
(c) Prat, D.; Wells, A.; Hayler, J.; Sneddon, H.; McElroy, C.R.; Abou-Shehada, S.; Dunn, P.J. Green Chem., 2016, 18(1), 288-296.
[http://dx.doi.org/10.1039/C5GC01008J]
[http://dx.doi.org/10.1080/23312009.2016.1154237]
[http://dx.doi.org/10.1021/acssuschemeng.6b01765]
[http://dx.doi.org/10.2174/221334610101131218094907];
(b) Tiwari, J.; Saquib, M.; Singh, S.; Tufail, F.; Singh, J. Singh. J. Synth. Commun., 2017, 47(21), 1999-2006.
[http://dx.doi.org/10.1080/00397911.2017.1359844]
[http://dx.doi.org/10.1016/j.apcatb.2015.04.030]
[http://dx.doi.org/10.1016/j.tet.2020.131059]
[http://dx.doi.org/10.1039/c4gc00451e]
[http://dx.doi.org/10.1039/C6RA10686B]
[http://dx.doi.org/10.1039/C5RA02794B];
(b) Nazeef, M.; Saquib, M.; Tiwari, S.K.; Yadav, V.; Ansari, S.; Sagir, H.; Hussain, M.K.; Siddiqui, I.R. ChemSelect, 2020, 5(45), 14447-14454.
[http://dx.doi.org/10.1039/C3GC41769G]
[http://dx.doi.org/10.1016/j.scp.2016.07.003]
[http://dx.doi.org/10.1016/j.molliq.2014.09.016];
(b) Yap, C.L.; Gan, S.; Ng, H.K. J. Environ. Sci., 2012, 24(6), 1064-1075.
[http://dx.doi.org/10.1016/S1001-0742(11)60873-5] [PMID: 23505874]
[http://dx.doi.org/10.1002/cssc.201901735] [PMID: 31412165]
[http://dx.doi.org/10.1111/j.1365-2621.2010.02496.x]
[http://dx.doi.org/10.1016/j.jbiosc.2014.06.003] [PMID: 25077706]
[http://dx.doi.org/10.1016/j.ejmech.2009.05.014] [PMID: 19525040]
[http://dx.doi.org/10.1007/s00044-011-9931-7]
[http://dx.doi.org/10.1016/j.ejmech.2013.08.032] [PMID: 24095752]
[http://dx.doi.org/10.1016/j.bmcl.2010.08.046] [PMID: 20813528]
[http://dx.doi.org/10.1016/S0968-0896(02)00128-1] [PMID: 12110323]
[http://dx.doi.org/10.1021/jm00170a015] [PMID: 2165161]
[http://dx.doi.org/10.1007/s00044-011-9943-3];
(b) Malik, A.A.; Dangroo, N.A.; Ara, T. ChemSelect, 2020, 5(42), 12965-12970.
[http://dx.doi.org/10.1021/jo00110a021]
[http://dx.doi.org/10.1080/17518253.2010.487841]
[http://dx.doi.org/10.1070/MC2005v015n04ABEH002123]
[http://dx.doi.org/10.1021/jo000711f] [PMID: 10987976]
[http://dx.doi.org/10.1021/jo301806n] [PMID: 23101501]
(b) El Maatougui, A.; Azuaje, J.; Gonzalez-Gomez, M.; Miguez, G.; Crespo, A.; Carbajales, C.; Escalante, L.; García-Mera, X.; Gutierrez-de-Teran, H.; Sotelo, E. J. Med. Chem., 2016, 59(5), 1967-1983.
(b) Mohamadpour, F. ACS omega, 2022, 7(10), 8429-8436.;
(c) Lulu, Z.; Yuqing, W.; Xiaogang, L.; Wenbin, Z. Chin. J. Org. Chem., 2022, 42(11), 3714.;
(d) Shekh, A.; Mombeni Goodajdar, B.; Asghariganjeh, M.R. Polycycl. Aromat. Compd., 2022, 42(8), 5649-5660.;
(e) Mass, E.B.; de Lima, C.A.; D’Oca, M.G.; Sciani, J.M.; Longato, G.B.; Russowsky, D. Drugs and Drug Candidates, 2022, 1(1), 3-21.;
(f) Salami, M.; Ezabadi, A. Lett. Org. Chem., 2022, 19(12), 1047-1061.;
(g) Yang, X.; Sun, H.; Maddili, S.K.; Li, S.; Yang, R.G.; Zhou, C.H. Eur. J. Med. Chem., 2022, 232, 114188.;
(h) Patel, P.N.; Patel, N.C.; Desai, D.H. Results. Chem, 2022, 4, 100362.;
(i) Gawhale, N.D.; Lokhande, M.N.; Uke, S.J.; Mardikar, S.P.; Pandit, V.U.; Kodape, M.M. Mater. Today Proc., 2022, 53, 191-195.;
(j) Houshiar, S.; Rafiee, Z.; Grami, M. Appl. Organomet. Chem., 2022, 36(9), e6800.;
(k) Moradi, S.; Moradian, M.; Naeimi, H. Acta Chim. Slov., 2022, 69(2)
(b) Chopda, L.V.; Dave, P.N. Arab. J. Chem., 2020, 13(6), 5911-5921.;
(c) V., Chopda L.; Dave, P.N. ChemistrySelect, 2020, 5(8), 2395-2400.;
(d) Tamaddon, F.; Arab, D. Ahmadi-AhmadAbadi. E. Carbohydr. Polym., 2020, 229, 115471.;
(e) Guo, Y.C.; Song, X.D.; Deng, W.; Rao, W.; Xu, H.; Shen, Z.L. RSC Advances, 2020, 10(50), 30062-30068.;
(f) Ali, G.; Dangroo, N.A.; Raheem, S.; Naqvi, T.; Ara, T.; Rizvi, M.A. Acta Chim. Slov., 2020, 67(1), 195-202.;
(g) Kheffache, O.; Lopez-Olmos, C.; Rodriguez-Ramos, I.; Cherifi, O. Bull. Chem. React. Eng. Catal., 2020, 15(3), 698-713.;
(h) Gadkari, Y.U.; Hatvate, N.T.; Takale, B.S.; Telvekar, V.N. New J. Chem., 2020, 44(20), 8167-8170.
(b) Wu, P.; Feng, L.; Liang, Y.; Zhang, X.; Mahmoudi, B.; Kazemnejadi, M. Appl. Catal. A Gen., 2020, 590, 117301.;
(c) Zhao, S.Y.; Chen, Z.Y.; Wei, N.; Liu, L.; Han, Z.B. Inorg. Chem., 2019, 58(12), 7657-7661.;
(d) Zarnaghash, N.; Rezaei, R.; Hayati, P.; Doroodmand, M.M. Mater. Sci. Eng. C, 2019, 104, 109975.
(b) Patel, H.A.; Sawant, A.M.; Rao, V.J.; Patel, A.L.; Bedekar, A.V. ChemistrySelect, 2017, 4(6), 1895-1902.
(b) Baranwal, J.; Kushwaha, S.; Singh, S.; Jyoti, A. Heterocyclic Lett., 2022, 12(3), 621-630.;
(c) Baranwal, J.; Singh, S.; Kushwaha, S.; Jyoti, A. Lett. Org. Chem., 2023, 20(5), 446-456.;
(d) Baranwal, J.; Kushwaha, S.; Singh, S.; Jyoti, A. Curr. Phys. Chem., 2023, 13(1), 2-19.;
(e) Kushwaha, S.; Baranwal, J.; Singh, S.; Jyoti, A. Curr. Green Chem., 2022, 9(3), 174-195.;
(f) Kushwaha, S.; Singh, S.; Baranwal, J.; Jyoti, A. Curr. Organocatal., 2023, 10(3), 215-224.;
(g) Kushwaha, S.; Singh, S.; Baranwal, J.; Jyoti, A. In: Stepping into the World of Technology; Research Culture Society and Publication, 2023, pp. 75-83.;
(h) Baranwal, J.; Singh, S.; Kushwaha, S.; Jyoti, A. In: Stepping into the World of Technology; Research Culture Society and Publication, 2023, pp. 63-74.;
(i) Tiwari, J.; Singh, S.; Jaiswal, D.; Sharma, A.K.; Singh, S.; Singh, J. Singh. J. Curr. Catal., 2020, 9(2), 92-101.
(b) Kolvari, E.; Koukabi, N.; Armandpour, O. Tetrahedron, 2014, 70(6), 1383-1386.
(b) Bosica, G.; Cachia, F.; De Nittis, R.; Mariotti, N. Molecules, 2021, 26(12), 3753.;
(c) Sahota, N.; AbuSalim, D.I.; Wang, M.L.; Brown, C.J.; Zhang, Z.; El-Baba, T.J.; Cook, S.P.; Clemmer, D.E. Chem. Sci., 2019, 10(18), 4822-4827.;
(d) Ghafoor, A.; Sajid, N.; Adnan, M.; Khan, M.N.; Abid, A.; Zafar, A.M.; Ahmad, M.; Aslam, N.; Jabeen, M.; Ali, A.; Khan, M.A. J. Heterocycl. Chem., 2020, 6(1), 1-5.
(b) Fekri, L.Z.; Nikpassand, M.; Movaghari, M. Bull. Chem. Soc. Ethiop., 2017, 31(2), 313-321.;
(c) Kolvari, E.; Koukabi, N.; Hosseini, M.M.; Vahidian, M.; Ghobadi, E. RSC Advances, 2016, 6(9), 7419-7425.;
(d) Javidi, J.; Esmaeilpour, M.; Dodeji, F.N. RSC Advances, 2015, 5(1), 308-315.