Efficient sonochemical green reaction of aldehyde, thiobarbituric acid and ammonium acetate using magnetically recyclable nanocatalyst in water

Ultrasonics Sonochemistry

Volumn 34, Issue , 2017, Pages 889-895

  Naeimi, Hossein ^a   Didar, Asieh ^a  

^a UNIVERSITY OF KASHAN   (Iran)

Author keywords

2 Thiobarbituric acid; Aldehyde; Dipyrimidine; Magnetic; Ultrasound

Indexed keywords

NANOCATALYSTS; ULTRASONICS;

2-THIOBARBITURIC ACID; DIPYRIMIDINE; ENVIRONMENTALLY BENIGN; HETEROGENEOUS CATALYST; MAGNETIC; MILD REACTION CONDITIONS; RECOVERABLE AND REUSABLE CATALYST; ULTRASOUND IRRADIATION;

ALDEHYDES;

ALDEHYDE; AMMONIUM ACETATE; MAGNETIC NANOPARTICLE; THIOBARBITURIC ACID; WATER;

ARTICLE; CONTROLLED STUDY; DRUG PURIFICATION; GREEN CHEMISTRY; IRRADIATION; MAGNET; NANOCATALYST; ONE POT SYNTHESIS; PRECIPITATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84982701864     PISSN: 13504177     EISSN: 18732828     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2016.07.021     Document Type: Article

References (42)

1. 3 supported sulfonic acid nanocatalyst under solvent-free conditions. Chin. Chem. Lett. 25 (2014), 1387–1391.
2. [2] Yang, L., Shi, D., Chen, S., Chai, H., Huang, D., Zhanga, Q., Li, J., Microwave-assisted synthesis of 2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones catalyzed by DBU in aqueous medium. Green Chem. 14 (2012), 945–951.
3. [3] Kovacs, J.A., Allegra, C.J., Swan, J.C., Parillo, J.E., Chabner, B.A., Masur, H., Potent antipneumocystis and antitoxoplasma activities of piritrexim, a lipid-soluble antifolate. Antimicrob. Agents Chemother. 32 (1988), 430–433.
4. [4] Trumpp-Kallmeyer, S., Rubin, J.R., Humblet, C., Hamby, J.M., Showalter, H.D.H., Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine Inhibitors. J. Med. Chem. 41 (1998), 1752–1763.
5. [5] Furukawa, K., Hasegawa, T., Preparation of pyrido[2,3-d]pyrimidine-2,4-di-one derivatives as antiasthmatics and antiallergics. Chem. Abstr., 124, 1996, 289568c.
6. [6] Kolla, V.E., Deyanov, A.B., Nazmetdinov, F.Y., Kashina, Z.N., Drovosekova, L.P., Investigation of the anti-inflammatory and analgesic activity of 2-substituted 1-aryl-6-carboxy(carbethoxy)-7-methyl-4-oxo-1, 4-dihydropyrido[2,3-d]pyrimidines. Pharm. Chem. J. 27 (1993), 635–636.
7. [7] Rosowsky, A., Mota, C.E., Queener, S.F., Synthesis and antifolate activity of 2,4-diamino-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine analogues of trimetrexate and piritrexim. J. Heterocycl. Chem. 32 (1995), 335–340.
8. [8] Ellingboe, J.W., Princeton, N.J., Substituted pyridopyrimidines and antihypertensives. Chem. Abstr., 124, 1996, 176134q.
9. [9] Connolly, C.J.C., Hamby, J.M., Schroeder, M.C., Barvian, M., Lu, G.H., Panek, R.L., Discovery and structure-activity studies of a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. Bioorg. Med. Chem. Lett. 7 (1997), 2415–2420.
10. [10] Corre, L.L., Girard, A.L., Aubertin, J., Radvanyi, F., Lasselin, C.B., Jonquoy, A., Mugniery, E., Mallet, L.L., Busca, P., Merrer, Y.L., Synthesis and biological evaluation of a triazole-based library of pyrido[2,3-d]pyrimidines as FGFR3 tyrosine kinase inhibitors. Org. Biomol. Chem. 8 (2010), 2164–2173.
11. [11] Rawal, R.K., Tripathi, R., Katti, S.B., Pannecouquec, C., Clercq, E.D., Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents. Bioorg. Med. Chem. 15 (2007), 3134–3142.
12. [12] Donkor, I.O., Klein, C.L., Liang, L., Zhu, N., Bradley, E., Clark, A.M., Synthesis and antimicrobial activity of 6,7-annulated pyrido[2,3-d]pyrimidines. J. Pharm. Sci. 84 (1995), 661–664.
13. [13] Deyanov, A.B., Niyazov, R.K., Nazmetdivov, F.Y., Syropyatov, B.Y., Kolla, V.E., Konshin, M.E., Synthesis and biological activity of amides and nitriles of 2-arylamino-5-carboxy(carbethoxy)-6-methylnicotinic acids and 1-aryl-6-carbethoxy-7-methyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines. Pharm. Chem. J. 25 (1991), 248–250.
14. [14] Pastor, A., Alajarin, R., Vaquero, J.J., Alvarez-Builla, J., Casa-Juana, M.F., Sunkel, C., Priego, J.G., Fonseca, I., Sanz-Aparicio, J., Synthesis and structure of new pyrido[2,3-d]pyrimidine derivatives with calcium channel antagonist activity. Tetrahedron 50 (1994), 8085–8098.
15. [15] Broom, A.D., Shim, J.L., Anderson, G.L., Pyrido[2,3-d]pyrimidines. IV. Synthetic studies leading to various oxopyrido[2,3-d]pyrimidines. J. Org. Chem. 41 (1976), 1095–1099.
16. [16] El-Gazzar, A.B.A., Hafez, H.N., Synthesis of 4-substituted pyrido[2,3-d]pyrimidin-4(1H)-one as analgesic and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 19 (2009), 3392–3397.
17. [17] Bystryakova, I.D., Burova, O.A., Chelysheva, G.M., Zhilinkova, S.V., Smirnova, N.M., Safonova, T.S., Synthesis and biological activity of pyridol[2,3-d]pyrimidines. Pharm. Chem. J. 25 (1991), 874–876.
18. [18] Monge, A., Martinez-Merino, V., Sanmartin, C., Fernandez, F.J., Ochoa, M.C., Berllver, C., Artigas, P., Fernandez-Alvarez, E., 2-Arylamino-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidines: synthesis and diuretic activity. Eur. J. Med. Chem. 24 (1989), 209–216.
19. [19] Cravotto, G., Cintas, P., Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem. Soc. Rev. 35 (2006), 180–196.
20. [20] Mason, T.J., Phillip, J., Applied sonochemistry – the uses of power ultrasound in chemistry and processing. 2002, Wiley-VCH, Weinheim, 43–167.
21. [21] Abdulla, R.F., Ultrasound in organic synthesis. Aldrichim. Acta 21 (1988), 31–42.
22. 2. Ultrason. Sonochem., 19, 2012, 642.
23. [23] Sreedhar, B., Reddy, P.S., Sonochemical synthesis of 1,4-disubstituted 1,2,3-triazoles in aqueous medium. Synth. Commun. 37 (2007), 805–812.
24. [24] Mosslemin, M.H., Nateghi, M.R., Rapid and efficient synthesis of fused heterocyclic pyrimidines under ultrasonic irradiation. Ultrason. Sonochem. 17 (2010), 162–167.
25. [25] Sabounchei, S.J., Ahmadi, M., Palladacycle phosphine complexes as homogeneous catalysts for the Heck cross-coupling reaction at low catalyst loading under aerobic conditions. Inorg. Chim. Acta 405 (2013), 15–23.
26. 2 nanoparticles: an efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines. Tetrahedron 68 (2012), 7827–7833.
27. [27] Sheykhan, M., Mohammadnejad, H., Akbari, J., Heydari, A., Superparamagnetic magnesium ferrite nanoparticles: a magnetically reusable and clean heterogeneous catalyst. Tetrahedron Lett. 53 (2012), 2959–2964.
28. [28] Fujita, K., Umeki, S., Yamazaki, M., Ainoya, T., Tsuchimoto, T., Yasuda, H., Magnetically recoverable osmium catalysts for dihydroxylation of olefins. Tetrahedron Lett. 52 (2011), 3137–3140.
29. [29] Deng, J., Mo, L.P., Zhao, F.Y., Zhang, Z.H., Liu, S.X., One-pot, three-component synthesis of a library of spirooxindole-pyrimidines catalyzed by magnetic nanoparticle supported dodecyl benzenesulfonic acid in aqueous media. ACS Comb. Sci. 14 (2012), 335–341.
30. 4 as an efficient and magnetically separable catalyst. Tetrahedron Lett. 54 (2013), 1738–1742.
31. [31] Wang, J., Xu, B., Sun, H., Song, G., Palladium nanoparticles supported on functional ionic liquid modified magnetic nanoparticles as recyclable catalyst for room temperature Suzuki reaction. Tetrahedron Lett. 54 (2013), 238–241.
32. 4 nanoparticles: an efficient catalyst for one-pot three-component synthesis of novel dicyanomethyl-2-oxoindolin-3-ylthiocarboxylic acids in a green solvent. Monatsh. Chem. 145 (2014), 1009–1015.
33. 4 nanocatalyst: an efficient catalyst for the green synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H) dione derivatives. J. Iran. Chem. Soc. 11 (2014), 1407–1419.
34. 4 nanoparticles as an efficient magnetically recoverable and reusable catalyst. Appl. Catal. A 467 (2013), 270–278.
35. [35] Naeimi, H., Rabiei, Kh., Sonocatalyzed facile and mild one pot synthesis of gem-dichloroaziridine derivatives under alkaline conditions. Ultrason. Sonochem. 19 (2012), 130–135.
36. [36] Ghahremanzadeh, R., Rashid, Z., Zarnani, A.-H., Naeimi, H., A facile one-pot ultrasound assisted for an efficient synthesis of 1H-spiro[furo[3,4-b]pyridine-4,30-indoline]-3-carbonitriles. Ultrason. Sonochem. 21 (2014), 1451–1460.
37. 4 under neutral conditions. Ultrason. Sonochem. 24 (2015), 150–154.
38. [38] Naeimi, H., Kiani, F., Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst. Ultrason. Sonochem. 27 (2015), 408–415.
39. [39] Kidwai, M., Mohan, R., Saxena, S., Solidsupported Hantzsch-Biginelli reaction for syntheses of pyrimidine derivatives. Russ. Chem. Bull., Int. Ed. 52 (2003), 2323–2326.
40. [40] Mohamed, M.S., Awad, S.M., Sayed, A.I., Synthesis of certain pyrimidine derivatives as antimicrobial agents and anti-inflammatory agents. Molecules 15 (2010), 1882–1890.
41. [41] Ghahremanzadeh, R., Rashid, Z., Zarnani, A.H., Naeimi, H., Inorganic–organic hybrid silica based tin complex as a novel, highly efficient and recyclable heterogeneous catalyst for the one-pot preparation of spirooxindoles in water. Dalton Trans. 43 (2014), 15791–15797.
42. [42] Naeimi, H., Nejadshafiee, V., Islami, M.R., Iron (III)-doped, ionic liquid matrix-immobilized, mesoporous silica nanoparticles: application as recyclable catalyst for synthesis of pyrimidines in water. Micropor. Mesopor. Mat. 227 (2016), 23–30.