An efficient synthesis of pyrimido[4,5-b]quinoline and indenopyrido[2,3-d]pyrimidine derivatives in the presence of Fe3O4@nano-cellulose/Sb (V) as a bio-based magnetic nano-catalyst

Document Type : Article

Authors

1 Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box 89195-741, Iran

2 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran

Abstract

In this study, an eco-friendly approach has been introduced for the synthesis of pyrimido[4,5-b]quinolones and indenopyrido[2,3-d]pyrimidines. This synthesis was done via a three component coupling of 6-amino-2-(methylthio)pyrimidin-4(3H)-one, 1,3-indanedione/dimedone and aromatic aldehydes using Fe3O4@nano-cellulose/Sb(V) as catalyst under solvent-free condition at 70 °C by electrical mortar-heater. The catalyst was separated from the reaction mixture by an external magnet and reused for subsequent reactions. The present procedure offers many advantages such as high yield, easy work-up, simple isolation of catalyst by external magnet and high reusability of the it. The structure of the obtained pyrimido[4,5-b]quinolones and indenopyrido[2,3-d]pyrimidines products were studied by FT-IR, 1H-NMR and 13C-NMR spectroscopic data.

Keywords


  • References: 

    • Gangjee, A., Adair, O., Queener, S.F. “Pneumocystis carinii and toxoplasma gondii dihydrofolate reductase inhibitors and antitumor agents:  synthesis and biological activities of 2,4-diamino-5-methyl-6-[(monosubstituted anilino)methyl]- pyrido[2,3-d]pyrimidines”, Med. Chem., 42(13), pp. 2447-2455 (1999).
    • Gangjee, A., Vasudevan, A., Queener, S.F., Kisliuk, R.L. “2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductasesˮ, Med. Chem., 39(7), pp. 1438-1446 (1996).
    • Hamby, J.M., Connolly, C.J.C., Schroeder, M.C., Winter, R.T., Showalter, H.D.H., Panek, R.L., Major, T.C., Olsewski, B., Ryan, M.J., Dahring, T.“ Structure−activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitos”, Med. Chem., 40(15), pp. 2296-2303 (1997).
    • Broom, A.D., Shim, J.L., Anderson, .L. “Pyrido[2,3-d]pyrimidines. Part iv. synthetic studies leading to various oxopyrido[2,3-d]pyrimidines”, Org. Chem., 41(7), pp. 1095-1099 (1976).
    • Grivsky, E.M., Lee, S., Sigel, C.W., Duch, D.S., Nichol, C.A. “Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidineˮ, Med. Chem., 23(3), pp. 327-329 (1980).
    • Quintela, J.M., Peinador, C., Botana, L., Estevez, M., Riguera, R. “Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidinesˮ, Med. Chem., 5(8), pp. 1543-1553 (1997).
    • El-Gazzar, A.R., Hafez, H.N. “Synthesis of 4-substituted pyrido[2,3-d]pyrimidin-4(1H)-one as analgesic and anti-inflammatory agentsˮ, Med. Chem. Lett., 19(13), pp. 3392-3397 (2009).
    • Matsumoto, J., Minami, S. “Pyrido[2,3-d]pyrimidine antibacterial agents. 3. 8-alkyl-and 8-vinyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxyli acids and their derivativesˮ, Med. Chem., 18(1), pp. 74-79 (1975).
    • Suzuki, N. “Synthesis of antimicrobial agents. Part v. synthesis and antimicrobial activities of some heterocyclic condensed 1,8-naphthyridine derivativesˮ, & Pharm. Bull., pp. 761-768 (1980).
    • Oakes, V., Rydon, H.N. “Polyazanaphthalenes. part iv. further derivatives of 1:3:5- and 1:3:8-triazanaphthaleneˮ, Chem. Soc., Resumed , pp. 4433-4438 (1956).
    • Degraw, J.I., Kisliuk, R.L., Gaumont, Y., Baugh, C.M. “Antimicrobial activity of 8-deazafolic acidˮ, Med. Chem., 17(4), pp. 470-471 (1974).
    • Hurlbert, B.S., Valenti, B.F., “Studies on condensed pyrimidine systems. part xxiv. the condensation of 2,4,6-triaminopyrimidine with malondialdehyde derivativesˮ, Med. Chem., 11(4), pp. 708-710 (1968).
    • Bazgir, A., Moammadi Khanaposhtani, M., Ghahremanzadeh, R., Abolhasani Soorki, A. “A clean, three-component and one-pot cyclo-condensation to pyrimidine-fused heterocycles”, R. Chim., 12(12), pp. 1287-1295 (2009).
    • Tanifum, E.A., Kots, A.Y., Choi, B., Murad, F., Gilbertson, S.R. “Novel pyridopyrimidine derivatives as inhibitors of stable toxin a (sta) induced cgmp synthesis”, Med. Chem. Lett., 19(11), pp. 3067-3071 (2009).
    • Khurana, J.M., Chaudhary, A., Nand, B., Lumb, A. “Mediated indium(III) chloride catalyzed synthesis of fused pyrimidines and pyrazoles”, Tetrahedron Lett., 53(24), pp. 3018-3022 (2012).
    • 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”, Saudi Chem. Soc., 20(5), pp. 570-576 (2016).
    • Nemati, F., Saeedirad, R. “Nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4,5-b]quinolones and indeno fused pyrido[2,3-d]pyrimidines in water”, Chem. Lett., 24, pp. 370-372(2013).
    • Mamaghani, R., Tabatabaeian, K., Araghi, R., Fallah, A., Hossein Nia, R. “An efficient, clean, and catalyst-free synthesis of fused pyrimidines using sonochemistry”, O Chem., 2014, pp. 1-9 (2014).
    • Jiang, S., Shen, M., Sheykhahmad, F.R. “Fe3O4@urea/HITh-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 7-aryl-8H-benzo[h]indeno- [1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d] pyrimidine derivatives” Open Chem., 18, pp. 648-662 (2020).
    • Gholami, A., Mokhtary, M., Nikpassand, “Glycolic acid-supported cobalt ferrite-catalyzed one-pot synthesis of pyrimido[4,5-b]quinoline and indenopyrido[2,3-d]pyrimidine derivatives” Appl. Organomet. Chem., 34(12), (2020).
    • Shirini, F., Safarpoor, M., Langarudi, N., Daneshvar, N., Jamasbi, N,. Irankhah-Khanghah, M. “Preparation and characterization of [H2 DABCO][ClO4]2 as a new member of DABCO-based ionic liquids for the synthesis of pyrimido[4,5-b]-quinoline and pyrimido[4,5-d]pyrimidine derivatives” Mol. Struct., 1161, pp. 366-382 (2018).
    • Zare, A., Lotfifar, N., Dianat, M. “Preparation, characterization and application of nano-[Fe3O4@-SiO2@R-NHMe2][H2PO4] as a novel magnetically recoverable catalyst for the synthesis of pyrimido[4,5-b]quinolines” Mol. Struct., 1211, pp. 128030 (2020).
    • Jalili, F., Zarei, M., Zolfigol, M.A., Rostamnia, S., Moosavi-Zare, A.R. “SBA-15/PrN(CH2PO3H2)2 as a novel and efficient mesoporous solid acid catalyst with phosphorous acid tags and its application on the synthesis of new pyrimido[4,5-bb]quinolones and pyrido[2,3-dd]pyrimidines via anomeric based oxidation” Mesopor. Mat. 294, pp. 109865 (2020).
    • Sepehrmansouria, H., Zareia, M., Zolfigola, M.A., Moosavi-Zareb, A.R., Rostamnia, S., Moradia, “Multilinker phosphorous acid anchored En/MIL-100(Cr) as a novel nanoporous catalyst for the synthesis of new N-heterocyclic pyrimido[4,5-b] quinolines” Mol. Catal., 481, pp. 110303 (2020).
    • Safajoo, N., Mirjalili, B.F. and Bamoniri, A. “A facile and clean synthesis of indenopyrido[2,3-d]pyrimidines in the presence of Fe3O4@NCs/Cu(II) as bio-Based magnetic nano-catalyst”, Aromat. Compd., Inpress (2019).
    • Hoseinikhah, S., Mirjalili, B.F. “Fe3O4@NCs/Sb(V): as a cellulose based nano-catalyst for the synthesis of 4h-pyrimido[2,1-b]benzothiazoles” Polycycl. Aromat. Compd., Inpress (2020).
    • Araghi, R., Mirjalili, B.F., Zamani, L., Khabnadideh, S., Zomorodian, K., Faghih, , Arabi, H. “Docking, Synthesis and evaluation of the antifungal activity of pyrimido[4,5-b]quinolinsˮ, Iran. J. Pharm. Res., 19(1), pp. 251-259 (2020).
    • Mohammadi Ziarani, G., Hosseini Nasab, N., Rahimifard, M., Abolhasani Soorki, A. “One-pot synthesis of pyrido[2,3-d]pyrimidine derivatives using sulfonic acid functionalized SBA-15 and the study on their antimicrobial activitiesˮ, Saudi Chem. Soc., 19(6), pp. 676-681 (2015).
    • Osanlou, F., Nemati, F., Sabaqian, S. “An eco-friendly and magnetized biopolymer cellulose-based heterogeneous acid catalyst for facile synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in waterˮ, Res. Chem., 43, pp. 2159-2174 (2017).
    • Shi, D., Ni, S., Yang, F., Shi, J.W., Dou, G., Li, X., Wang, X., Ji, Sh. “An efficient synthesis of pyrimido[4,5‐b]quinoline and indeno[2′,1′:5,6]pyrido[2,3‐d]pyrimidine derivatives via multicomponent reactions in ionic liquidˮ, Heterocycl. Chem., 45(3), pp. 693-702 (2008).