全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Novel ZrOCl2·8H2O-Catalysed One-Pot Multicomponent Synthesis of 9,10-Dihydro-8H-benzo[a]xanthen-11(12H)-one Derivatives

DOI: 10.1155/2013/978397

Full-Text   Cite this paper   Add to My Lib

Abstract:

A simple and efficient protocol for the synthesis of highly substituted xanthenes is developed through the condensation of β-naphthol, aldehydes, and cyclic 5,5-dimethylcyclohexane-1,3-dione with zirconium oxychloride octahydrate as a catalyst via multicomponent condensation strategy. The present method gives good to excellent yields of substituted 9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one derivatives. 1. Introduction Xanthenes and benzoxanthenes are biologically important drug intermediates. They are cited as active oxygen hetero-cycles possessing antibacterial. Research on xanthenes, especially benzoxanthenes, has emerged in organic synthesis due to their wide range of biological and therapeutic properties like antiviral [1], antibacterial [2], and anti-inflammatory activities [3], as well as in photodynamic therapy [4] and as antagonists of the paralyzing action of zoxazolamine [5]. Xanthenes are also available from natural sources. Popularly known, Santalin pigments have been isolated from a number of plant species [6]. Furthermore, due to their useful spectroscopic properties, they are used as dyes [7], in laser technologies [8], and in fluorescent materials for visualization of biomolecules [9]. Many procedures are disclosed to synthesize xanthenes and benzoxanthenes like cyclodehydrations [10], trapping of benzynes by phenols [11], alkylations of hetero atoms [12], and cyclocondensations between 2-hydroxy aromatic aldehydes and 2-tetralone [13]. Benzaldehydes and acetophenones bearing tethered carbonyl chains underwent the intermolecular phenyl-carbonyl coupling reactions in the presence of samarium diiodide and hexamethylphosphoramide to afford xanthenes [14]. In addition, 14H-dibenzo[a,j]xanthenes and related products are prepared by reaction of β-naphthol with form amide [15], 1-hydroxy methyl-naphthalen-2-ol [16], and carbon monoxide [17]. Initially, we investigated the condensation reaction of β-naphthol, benzaldehyde, and 5,5-dimethylcyclohexane-1,3-dione using different Lewis acids catalysts and conditions such as La(OTf)3, ZnCl2, AlCl3, and Sr(OTf)3 [18]. However, many of these reagents or catalysts are expensive, harmful, and difficult to handle especially on a large scale. 2. Experimental 2.1. Materials and Instruments All reagents were purchased from Merck. Aldehydes were distilled before use. Melting points were determined using a Linkman HF591 heating stage, used in conjunction with a TC92 controller, and re-uncorrected. NMR spectra were recorded using either a Brucker DRX500 machine at room temperature. 1H, 13C NMR, and 19F NMR

References

[1]  R. W. Lambert, J. A. Martin, J. H. Merrett, K. E. B. Parkes, and G. J. Thomas, PCT International Application W0 9706178, Chemical Abstract 126, 212377y. 1997.
[2]  T. Hideo, Jpn Tokkyo Koho JP 56005480, Chemical Abstract, 95, 95, 1981.
[3]  J. P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, and R. Lacroix, “Synthesis and antiinflammatory properties of bis (2-hydroxy-1-naphthyl)methane derivatives I,” European Journal of Medicinal Chemistry, vol. 13, pp. 67–71, 1978.
[4]  R. M. Ion, Progr. Catal., vol. 2, p. 55, 1997.
[5]  G. Saint-Ruf, A. De, and H. T. Hieu, Bull. Chim. Ther, vol. 7, p. 83, 1972.
[6]  B. Ravindranath and T. R. Seshadri, “Structural studies on santalin permethyl ether,” Phytochemistry, vol. 12, no. 11, pp. 2781–2788, 1973.
[7]  A. Banerjee and A. K. Mukherjee, “Chemical aspects of santalin as a histological stain,” Stain Technology, vol. 56, no. 2, pp. 83–85, 1981.
[8]  O. Sirkeeioglu, N. Talinli, and A. Akar, Journal of Chemical Research, p. 502, 1995.
[9]  C. G. Knight and T. Stephens, “Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles,” Biochemical Journal, vol. 258, no. 3, pp. 683–689, 1989.
[10]  A. Bekaert, J. Andrieux, and M. Plat, “New total synthesis of bikaverin,” Tetrahedron Letters, vol. 33, no. 20, pp. 2805–2806, 1992.
[11]  D. W. Knight and P. B. Little, “The first high-yielding benzyne cyclisation using a phenolic nucleophile: a new route to xanthenes,” Synlett, no. 10, pp. 1141–1143, 1998.
[12]  R. Vazquez, M. C. de la Fuente, L. Castedo, and D. DomInguez, “A short synthesis of (±)-clavizepine,” Synlett, vol. 1994, no. 6, pp. 433–434, 1994.
[13]  A. Jha and J. Beal, “Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone,” Tetrahedron Letters, vol. 45, no. 49, pp. 8999–9001, 2004.
[14]  C. -W. Kuo and J. -M. Fang, “Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl–carbonyl coupling reactionss,” Synthetic Communications, vol. 31, no. 6, pp. 877–892, 2001.
[15]  P. Papini and R. Cimmarusti, “The action of formamide and formanilide on naphthols and on barbituric acid,” Gazzetta Chimica Italiana, vol. 77, pp. 142–147, 1947.
[16]  R. N. Sen and R. N. Sarkar, “The condensation of primary alcohols with resorcinol and other hydroxy aromatic compounds,” Journal of the American Chemical Society, vol. 49, no. 47, pp. 1079–1091, 1925.
[17]  K. Ota and T. Kito, “An improved synthesis of dibenzoxanthene,” Bulletin of the Chemical Society of Japan, vol. 49, no. 4, pp. 1167–1168, 1976.
[18]  J. Li, W. Tang, L. Lu, and W. Su, “Strontium triflate catalyzed one-pot condensation of β-naphthol, aldehydes and cyclic 1,3-dicarbonyl compounds,” Tetrahedron Letters, vol. 49, no. 50, pp. 7117–7120, 2008.
[19]  S. H. Mashraqui, M. B. Paul, H. D. Mistry, S. Ghadigaonkar, and A. Meetsma, “A three-component reaction of phenol, aldehyde, and active methylene substrate under Lewis acid catalysis: successful trapping of o-quinone methide to afford benzopyran systems,” Chemistry Letters, vol. 33, no. 8, pp. 1058–1059, 2004.

Full-Text

Contact Us

[email protected]

QQ:3279437679

WhatsApp +8615387084133