A new approach to the facile synthesis of 1,8-dioxooctahydroxanthene using nano-TiO2/ CNT as an efficient catalyst

Document Type : Research Article

Authors

Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

Abstract

1,8-dioxooctahydroxanthene derivatives have received considerable attention due to their valuable biological and medicinal properties such as anticoagulant, antispasmodic, diuretic, and anti-cancer activities. 1,8-dioxooctahydroxanthene derivatives have strong relaxing activity on blood vessels, cardiac muscles, and smooth muscles. The present study reports the easy synthesis of 1,8-dioxooctahydroxanthene derivatives using aldehydes and dimedon in the presence of nano-TiO2/ CNT as an efficient catalyst.

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  • (a) K. M. Khan, G. M. Maharvi, M. T. H. Khan, A. J. Shaikh, S. Perveen, M. I. Choudhary, Tetraketones: A new class of tyrosinase inhibitors. Bioorganic & Medicinal Chemistry, 14 (2006), 344-351; (b) C Av┼čar, D Tümük, S Ertunç, AO Gezerman, A Review on Ammono-Carbonation Reactions: Focusing on the Merseburg Process, Rev. Lett., 5 (2022) 83-91. DOI: 10.22034/crl.2022.329067.1154.
  • Carlin, R. Djursater, G. Smedegard, B. Gerdin, The enhancing effect of cyclosporine A and sulfasalazine. Agents Actions, 16(1985 ), 377-384.
  • W. Lambert, J.A. Martin, J.H. Merrett, B.K. Parkes, G.J. Thomas, Multicomponent synthesis of novel azo-linked xanthene. PCT Int Appl WO9706178 (1997) .
  • Hideo, B. Teruomi, Synthesis of Spiro [oxindole-benzo [a] xanthen]. J. Jpn Patent 56005480 (1981) .
  • Vereshchagin, M. N. Elinson, E. O. Dorofeeva , T. A.

 Zaimovskaya, N. O. Stepanov, S. V. Stepanov, P. A. Gorbunov, G. I. Belyakov,  .Electrocatalytic and chemical assembling of N,N′-dialkylbarbituric acids and aldehydes: efficient cascade approach to the spiro-[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′H,3H,3′H)-pentone framework. Tetrahedron, 68 (2012), 1198-1206.

  • K. Schwaebe, T. J. Moran, J. P. Whitten, Total synthesis of psorospermin. Tetrahedron Lett 46 ( 2005), 827-829.
  • Srihari, S.S. Mandal, J.Reddy, Synthesis of 1,8-dioxo-octahydroxanthenes utilizing PMA-SiO2 as an efficient reusable catalyst. Chin .Chem. Lett, 19( 2008) , 771.
  • Kantevari, R. Bantu, L. Nagarapu, HClO4–SiO2 and PPA–SiO2 catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free conditions: Scope and limitations. Journal of Molecular Catalysis A: Chemistry. 269( 2007) 53-59.
  • -S. Jin, J.-S. Zhang, A.-Q. Wang,T.-S. Li, Solid-state condensation reactions between aldehydes and 5,5-cyclohexanedione by grinding at room temperature. Synthetic Communications. 35( 2005) , 2339-2345.
  • Pabbaraja, Synthesis of 1, 8-dioxo-octahydroxanthenes utilizing PMA-SiO2 as an efficient reusable. Chinese Chemical Letters. 19 (2008), 771-777.
  • Hideo, Benzopyrano[2,3-b]xanthene derivatives, Chemical Abstract, 95(1981), 80922b.
  • P. Poupelin, G. Saint-Ruf, Foussard-Blanpin, O.; Narcisse, G.; Uehida, G.; Lacroix, R. A general synthetic route to 1,8-dioxo-octahydroxanthenes has been developed using tetrabutylammonium hydrogen sulfate. European Jouranal of Medical Chemistry. 13(1978), 67-61.
  • Saint-Ruf, H.T. Hieu, synthesis of 1, 8-dioxo-octahydroxanthenes using DABCO- bromine. Bulletin of the Chemical Society of Japan. 7(1972), 83-86.
  • Cvetkovic, J. Adrie, J. Straathof, K. Rajamani, A.M. Luuk, Adsorption of Xanthene Dyes by Lysozyme Crystals. Derwielen. Langmuir. 21(2005), 1475-1478.
  • F. Callan, P. De Silva, D.C. Magri, Luminescent sensors and switches in the early 21st century. Tetrahedron 61(2005), 8551-8588.                        

 

 

 

Volume 5, Issue 4 - Serial Number 4
August 2022
Pages 268-277
  • Receive Date: 06 May 2022
  • Revise Date: 19 July 2022
  • Accept Date: 20 July 2022
  • First Publish Date: 20 July 2022