One Pot, Solvent-Free, and Efficient Synthesis of Tetrahydrobenzo[α]xamthene-11-One Derivatives using Nano- CeO2 as a Recyclable Catalyst

Document Type : Research Paper

Authors

Department of chemistry, Payame Noor University (PNU), P.O. Box 19395-4697, Tehran, Iran

Abstract

Xanthene and its derivatives have extensive biological properties and they are used in the pharmaceutical industry. Due to the spectral properties of these compounds, they are also used in the dye industry and due to their photochemical-photophysical properties in laser technology. Due to the importance of these compounds, in this study, the synthesis of tetrahydrobenzo [α] xanthine-11-one derivatives was investigated through a three-component reaction of benzaldehyde, dimedon and 2-naphthol derivatives using cerium oxide nanoparticle catalyst under solvent-free conditions is located. Non-use of environmentally harmful solvents, high speed and short reaction time, high product efficiency and recyclability of the catalyst are the advantages of the present method.

Keywords


[1] Kulesza A EFH, Mishra R.K, Cross-Doersen D, Mazur A.W. Organic Lett. 2003;5:1163.
 
[2] Redman A.M DJ, Scott W. J Org Lett. 2000;6:767.
 
[3] Sanchez F HPC, Cruz  Y, alcaraz J, Tamariz  F, Delgado, Vazquez M.A. J Mex Chem Soc. 2012;56:121.
 
[4] Hafez E.A EMH, Elagemey A.G.A, El-Taweel F.M.A.A. Heterocycles. 1987;26:903.
 
[5] Seshu Babu N PN, Wara Rao V, Sai Prasad T,  Lingaiah P.S. Tetrahedron Lett. 2008;49:2730-3.
[1] Partoie T SA. Synthesis and antibacterial activity of nitroaryl thiadiazole-gatifloxacin hybrids. European journal of medicinal chemistry. 2009;3:1768-3254.
 
[2] Goodell J.R P-BF, Forshey B.M, Shi P.Y, Ferguson D.M. Identification of compounds with anti-West Nile virus activity. Journal of medicinal chemistry. 2006;49:2127-37.
 
[3] Griffiths J LWJ. Multicomponent, solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives catalysed by cyanuric chloride. Dyes Pigment. 2003;57:107-12.
 
[4] Knight C.G ST. Xanthene-dye-labelled Phosphatidylethanolamines as Probes of Interfacial pH. Studies in Phospholipid Vesicles. Biochemistry Journal. 1989;258:683-9.
 
[5] Kumar P. S KBS, Reddy P. N, Sreenivasulu N, Reddy T. A novel one pot synthesis of 14-aryl-14H-dibenzo [a, j] xanthenes catalyzed. Arkivok. 2006;xii:46-50.
 
[6] Neckers D.C V-AOM. Photochemistry of the Xanthine Dyes. Advanced Photochemistry. 1993;18:315.
 
[7] John A. J MK. Heterocyclic Chemistry, 5th Edition. Wiley. 2010;718:978.
 
[8] Naeimi H NZS. Sulfonated diatomite as heterogeneous acidic nanoporous catalyst for synthesis of 14-aryl-14-H-dibenzo [a, j] xanthenes under green conditions. Applied Catalysis A:General. 2014:132-9.
 
[9] Oskooie H. A HMM, Karimi N, Kohansal G. Cu/SiO2-Catalyzed One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[α]xanthen-11-ones Under Solvent-Free Conditions. Synthetic Communications. 2011;41:2763-9.
 
[10] Shirini F AM, Pourhasan R. N-sulfonic acid poly (4-vinylpyridinium) chloride: A novel polymeric and reusable catalyst for the preparation of xanthenes derivatives Dyes Pigment. 2013;99:250-8.
 
[11] Gunjegaonkar M. B FSA, Kolhe R. C. Synthesis and biological evaluation of xanthen-1, 8-dione derivatives. International Journal of Research in Pharmacy and Chemistry. 2018;8:319-23.
 
[12] Yang Y EJO. A convenient preparation of xanthene dyes. Journal of Organic Chemistry. 2008;70:6907-13.
 
[13] Shirni F YA, Mohammadi K. One-pot synthesis of various xanthene derivatives using ionic liquid 1, 3-disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable catalyst. Chinese Chemical Letters. 2014;24:341-8.
 
[14] Shrin F A-DS, Mohammad-Khah A, Aliakbar A-R. Rice husk: a mild, efficient, green and recyclable catalyst for the synthesis of 12-Aryl-8, 9, 10, 12-tetrahydro [a] xanthene-11-ones and quinoxaline derivatives. Comptes Rendus Chimie. 2013;16:207.
 
[15] Nemati F SS, Mild. highly efficient method for the oxidation of sulfides and oxidative coupling of thiols catalyzed by Fe3O4@MCM-41@VO-SPATB as efficient and magnetically catalyst. Journal of Saudi Chemical Society. 2014;21:383-9.
 
[16] Taghavi F GM, Saljooghi S. A, Ramezani M. Metal free synthesis of tetrahydrobenzo [a] xanthenes using orange peel as a natural and low cost efficient heterogeneous catalyst. Comptes Rendus Chimie. 2016;6:870822-87088.
 
[17] Ghorbani-Vaghei R MSM. Facile One-Pot Synthesis of Tetrahydrobenzo[a]xanthene-11-one and Aryl-14H-dibenzo[aj]xanthene. Organic preparation and Procedures Internationals. 2010;42:494-7.
 
[18] Preetam A PD, Sharma K. J, Nath M. GREEN FARMING. Current Microwave Chemistry. 2015;2:15-23.
 
[19] Shinde V. P KHA, Shingate B. B, Shingare S. M,. Silica in water: a potentially valuable reaction medium for the synthesis of pyrano [2, 3-c] pyrazoles. Belistein Journal of Organic Chemistry. 2011;7:53-8.
 
[20] Pouramiri B SM, Tavakolinejad Kermani E. Facile and rapid synthesis of divers xanthene derivatives using Lanthanum (III) chloride/chloroacetic acid as an efficient and reusable catalytic system. Journal of the Serbian Chemical Society. 2017;82:483-7.
 
[21] Sudha S PMA. Ultrasound assisted synthesis of tetrahydrobenzo [c] xanthene-11-ones using CAN as catalyst. Ultrasonics Sonochemistry. 2012;19:994-8.
 
[22] Singh H KS, Khurana M. J. A new green approach for the synthesis of 12-aryl-8, 9, 10, 12-tetrahydrobenzo [a] xanthene-11-one derivatives using task specific acidic ionic liquid [NMP] H2PO4. Chinese Chemical Letters. 2014;25:1336-9.
 
[23] Shitole V. N SSB, Shingate B. B, Shingare S. M. Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde. Bulletin of the Korean Chemical Society. 2011;32:35-9.
 
[24] F M. Synthesis of Quinolines. Spiro[4H-pyran-oxindoles] and Xanthenes Under Solvent-Free Conditions. 2017;53:449-54.
 
[25] M H-S. Catalytic Organic Reactions on ZnO. Journal of Synthetic Organic Chemistry. 2008;38:832-7.
 
[26] Khodaei A.R KMH. A Facile Simple and convenient method for the synthesis of 14‐alkyl or aryl‐14‐H‐dibenzo [a, j] xanthenes catalyzed by p‐TSA in solution. Journal of the Iranian Chemical Society. 2006;41:916-26.
 
[27] Kaspar J FP, Graziani M. Use of CeO2-based oxides in the three-way catalysis. Catalysis Today. 1999;50:285-91.
 
[28] Yin X HL, Liu Z.L. Oxygen permeation through the LSCO-80/CeO2 asymmetric tubular membrane reactor. Journal of Membrane Science. 2006;268:2-10.
 
[29] Park S.D VJM, Gorte RJ. Direct oxidation of hydrocarbons in a solid-oxide fuel cell. Nature. 2000;404:265-71.
 
[30] N O. Optical properties and electrochromic characterization of sol–gel deposited ceria films. Solar Energy Materials and Solar Cells. 2001;68:391-8.
 
[31] Asati A SS, Kaittanis C, Nath S, Perez J.M. Oxidase‐like activity of polymer‐coated cerium oxide nanoparticles. Angewandte Chemie International Edition. 2009;48:2308-12.
 
[32] Mazaheri M H-TSA, Aminzare M, Sadrnezhaad S.K. Proceedings of the 11th ECERS Conference Krakow. 2009. p. 655.
 
[33] Prasad D PA, Nath M. Microwave-assisted green synthesis of dibenzo [a, j] xanthenes using p-dodecylbenzenesulfonic acid as an efficient Bronsted acid catalyst under solvent-free. Comptes Rendus Chimie. 2012;15:675-9.
 
[34]  1961-11-01  C-P-d.
 
[35] Zieve D MM, Oglivie Isla, PhD and the A. D. A. MK Editorial Team, https://medlineplus.gov/ency/article/002406.com, 2015.