Sulfonated organic heteropolyacid salts as a highly efficient and green solid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives in water

Arabian Journal of Chemistry

Volumn 12, Issue 7, 2019, Pages 1515-1521

  Vahdat, Seyed Mohammad ^a   Khaksar, Samad ^a   Akbari, Maryam ^a   Baghery, Saeed ^a,b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b BU ALI SINA UNIVERSITY   (Iran)

Author keywords

1,8 Dioxo decahydroacridine; Green solid acid catalyst; Ionic liquid; One pot synthesis; Water solvent

Indexed keywords

AMINES; AROMATIC COMPOUNDS; IONIC LIQUIDS; REUSABILITY;

1,8-DIOXO-DECAHYDROACRIDINE; AROMATIC ALDEHYDE; HETEROPOLYACID SALTS; MILD REACTION CONDITIONS; ONE-POT SYNTHESIS; SOLID ACID CATALYSTS; THREE COMPONENT REACTIONS; WATER SOLVENTS;

CATALYSTS;

EID: 84963990898     PISSN: 18785352     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.arabjc.2014.10.026     Document Type: Article

References (39)

1. Antonini, I., Polucci, P., Kelland, L.R., Menta, E., Pescalli, N., Martelli, S., 2,3-Dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione derivatives, a class of cytotoxic agents active on multidrug-resistant cell lines: synthesis, biological evaluation, and structure-activity relationships. J. Med. Chem. 42 (1999), 2535–2541.
2. Bakibaev, A.A., Fillimonov, V.D., Nevgodova, E.S., Reactions of 1,3-dicarbonyls with azomethines and urea in DMSO as a method for the synthesis of aryl-substituted acridine-1,8-diones and 1,4-dihydropyridines. Zh. Org. Khim. 27 (1991), 1519–1524.
3. Balalaie, S., Chadegan, F., Darviche, F., Bijanzadeh, H.R., One-pot synthesis of 1,8-dioxo-decahydroacridine derivatives in aqueous media. Chin. J. Chem. 27 (2009), 1953–1956.
4. Berkan, O., Sarac, B., Simsek, R., Yildirim, S., Sariogli, Y., Safak, C., Vasorelaxing properties of some phenylacridine type potassium channel openers in isolated rabbit thoracic arteries. Eur. J. Med. Chem. 37 (2002), 519–523.
5. Bhatnagar, D., Kidwai, M., Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-1,8-diones in PEG. Tetrahedron Lett. 51 (2010), 2700–2703.
6. Bossert, F., Vater, W., 1,4-Dihydropyridines – a basis for developing new drugs. Med. Res. Rev. 9 (1989), 291–324.
7. Chandrasekhar, S., Rao, Y.S., Sreelakshmi, L., Mahipal, B., Reddy, C.R., Tris(pentafluorophenyl)borane-catalyzed three-component reaction for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions. Synthesis 11 (2008), 1737–1740.
8. Dabiri, M., Baghbanzadeh, M., Arzroomchilar, E., 1-Methylimidazolium trifluoroacetate ([Hmim]TFA): an efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines. Catal. Commun. 9 (2008), 939–942.
9. Das, B., Thirupathi, P., Mahender, I., Reddy, V.S., Rao, Y.K., Amberlyst-15: an efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines. J. Mol. Catal. A: Chem. 247 (2006), 233–239.
10. Fang, F., Tu, S.J., Zhu, S., Li, T., Zhang, X., Zhuang, Q., One-pot synthesis of a novel compound N-hydroxydecahydroacridine under microwave irradiation. J. Heterocycl. Chem. 41 (2004), 767–770.
11. Gallo, S., Atifi, S., Mohamoud, A., Santelli-Rouvier, C., Wolfart, K., Molnar, J., Barbe, J., Synthesis of aza mono, bi and tricyclic compounds. Evaluation of their anti MDR activity. Eur. J. Med. Chem. 38 (2003), 19–26.
12. Gamega, S.A., Spicer, J.A., Atwell, G.J., Finlay, G.J., Baguley, B.C., Deny, W.A., Structure-activity relationships for substituted bis(acridine-4-carboxamides): a new class of anticancer agents. J. Med. Chem. 42 (1999), 2383–2393.
13. Islam, A., Murugan, P., Hwang, K.C., Cheng, C.H., Blue light-emitting devices based on 1,8-acridinedione derivatives. Synth. Met. 139 (2003), 347–353.
14. Jin, T.S., Zhang, J.S., Guo, T.T., Wang, A.Q., Li, T.S., One-pot clean synthesis of 1,8-dioxo-decahydroacridines catalyzed by p-dodecylbenzenesulfonic acid in aqueous media. Synthesis 12 (2004), 2001–2005.
15. Kaya, M., Yildirir, Y., Celik, Y.G., Synthesis and antimicrobial activities of novel bisacridine-1,8-dione derivatives. Med. Chem. Res. 20 (2011), 293–299.
16. Khalafi-Nezhad, A., Mokhtari, B., Tetrabutylammonium bromide: an efficient media for dimethoxytritylation of the 5′-hydroxyl function of nucleosides. Tetrahedron Lett. 45 (2004), 6737–6739.
17. Kidwai, M., Bhatnagar, D., Polyethylene glycol-mediated synthesis of decahydroacridine-1,8-diones catalyzed by ceric ammonium nitrate. Chem. Pap. 64 (2010), 825–828.
18. Lacassagne, A., Buu-Ho, N.P., Daudel, R., Zajdela, F., The relation between carcinogenic activity and the physical and chemical properties of angular benzacridines. Adv. Cancer Res. 4 (1956), 315–369.
19. Li, C.J., Chan, T.H., Organic Reaction in Aqueous media. 1997, Wiley, New York.
20. Li, Y.L., Zhang, M.M., Wang, X.S., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., One-pot three-component synthesis of 9-arylpolyhydroacridine derivatives in an ionic liquid medium. J. Chem. Res. (S), 2005, 600–602.
21. Martin, N., Quinteiro, M., Seoane, C., Soto, J.L., Mora, A., Suarez, M., Morales, A., Ochoa, E., Bosque, J.D., Synthesis and conformational study of acridine derivatives related to 1,4-dihydropyridines. J. Heterocycl. Chem. 32 (1995), 235–238.
22. Miao, C.B., Tu, S.J., Gao, Y., Feng, Y.J., Feng, J.C., Microwave-prompted reaction of cinnamonitrile derivatives with 5,5-dimethyl-1,3-cyclohexanedione. Chin. J. Chem. 20 (2002), 703–706.
23. Mikata, Y., Yokoyama, M., Mogami, K., Kato, M., Okura, I., Chikira, M., Yano, S., Intercalator-linked cisplatin: synthesis and antitumor activity of cis-dichloroplatinum (II) complexes connected to acridine and phenylquinolines by one methylene chain. Inorg. Chim. Acta 279 (1998), 51–57.
24. Murugan, P., Shanmugasundaram, P., Ramakrishnan, V.T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K., Velmurugan, D., Synthesis and laser properties of 9-alkyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives. J. Chem. Soc. Perkin Trans. 2:4 (1998), 999–1004.
25. Ngadi, L., Galy, A.M., Galy, J.P., Barbe, J., Cremieux, A., Chevalier, J., Sharples, D., Some new 1 – nitro acridine derivatives as antimicrobial agents. Eur. J. Med. Chem. 25 (1990), 67–70.
26. Shen, W., Wang, L.M., Tian, H., Tang, J., Yu, J.J., Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water. J. Fluor. Chem. 130 (2009), 522–527.
27. Spalding, D.P., Chapin, E.C., Mosher, H.S., Heterocyclic basic compounds. XV. Benzacridine derivatives. J. Org. Chem. 19 (1954), 357–364.
28. Suárez, M., Loupy, A., Salfrán, E., Morán, L., Rolando, E., Synthesis of decahydroacridines under microwaves using ammonium acetate supported on alumina. Heterocycles 51 (1999), 21–27.
29. Tu, S.J., Lu, Z., Shi, D., Yao, C., Gao, Y., Guo, C., A convenient synthesis of 9-aryl-3,3,6,6,-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under microwave irradiation without solvent. Synth. Commun. 32 (2002), 2181–2185.
30. Tu, S.J., Miao, C., Gao, Y., Fang, F., Zhuang, Q., Feng, Y., Shi, D., Novel cascade reaction of aryl aldoxime with dimedone under microwave irradiation: the synthesis of N-hydroxylacridine. Synlett 2 (2004), 255–258.
31. Venkatesan, K., Pujari, S.S., Srinivasan, K.V., Proline-catalyzed simple and efficient synthesis of 1,8-dioxo-decahydroacridines in aqueous ethanol medium. Synth. Commun. 39 (2009), 228–241.
32. Wainwright, M., Acridine – a neglected antibacterial chromophore. J. Antimicrob. Chemother. 47 (2001), 1–13.
33. Wang, X.S., Shi, D.Q., Wang, S.H., Tu, S.J., Synthesis of 9-aryl-10-(4-methylphenyl)polyhydroacridine under microwave irradiation. Chin. J. Org. Chem. 23 (2003), 1291–1293.
34. Wang, X.S., Shi, D.Q., Zhang, Y.F., Wang, S.H., Tu, S.J., Synthesis of 9-arylpolyhydroacridine in water catalyzed by triethylbenzylammonium chloride (TEBA). Chin. J. Org. Chem. 24 (2004), 430–432.
35. Wang, J., Leng, Y., Zhu, D., Ren, X., Ge, H., Shen, L., Heteropolyanion-based ionic liquids: reaction-induced self-separation catalysts for esterification. Ang. Chem. Int. Ed. 48 (2009), 168–171.
36. Wasserscheid, P., Keim, W., Ionic liquids-new ‘solutions’ for transition metal catalysis. Ang. Chem. Int. Ed. 39 (2000), 3772–3789.
37. Welton, T., Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99 (1999), 2071–2084.
38. Welton, T., Ionic liquids in catalysis. Coord. Chem. Rev. 248 (2004), 2459–2477.
39. Zhang, M.M., Wang, X.S., Jiang, H., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., An improved and benign synthesis of 9,10-diarylacridine-1,8-dione and indenoquinoline derivatives from 3-anilino-5,5-dimethylcyclohex-2-enones, benzaldehydes, and 1,3-dicarbonyl compounds in an ionic liquid medium. Synthesis 24 (2006), 4187–4199.