Molecular Diversity

, Volume 14, Issue 4, pp 621–626 | Cite as

Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]-dioxolo [4,5- b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones

Full-Length Paper

Abstract

Three-component one-pot synthesis of some novel 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]-dioxolo[4,5-b]xanthen-9-ones, which have not been published before, and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones from condensation of 3,4-methylenedioxyphenol or β-naphthol, aldehydes and dimedone under solvent-free conditions at 120 °C is reported.

Keywords

Sulfamic acid Dioxolo-[4,5-b]xanthene-9-ones Benzo[a]xanthenes Solvent-free reactions 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Hafez HN, Hegab MI, Ahmed-Farag IS, El-Gazzar ABA (2008) A facile regioselective synthesis of novel spiro-thioxanthene and spiro-xanthene-9′,2-[1,3,4]thiadiazole derivatives as potential analgesic and anti-inflammatory agents. Bioorg Med Chem Lett 18: 4538–4543. doi:10.1016/j.bmcl.2008.07.042 CrossRefPubMedGoogle Scholar
  2. 2.
    Li J, Tang W, Lu L, Su W (2008) Strontium triflate catalyzed one-pot condensation of β-naphthol, aldehydes and cyclic 1,3-dicarbonyl compounds. Tetrahedron Lett 49: 7117–7120. doi:10.1016/j.tetlet.2008.09.129 CrossRefGoogle Scholar
  3. 3.
    Menchen SM, Benson SC, Lam JYL, Zhen W, Sun D, Rosenblum BB, Khan SH, Taing M (2003) Sulfonated diarylrhodamine dyes. US Patent 6583168Google Scholar
  4. 4.
    Sarma RJ, Baruah JB (2005) One step synthesis of dibenzoxanthenes. Dyes Pigment 64: 91–92. doi:10.1016/j.dyepig.2004.03.010 CrossRefGoogle Scholar
  5. 5.
    Khosropour AR, Khodaei MM, Moghannian H (2005) Condensations of β-naphthol with aldehydes in the presence of a catalyst like p-TSA. Synlett 955–958. doi:10.1055/s-2005-864837
  6. 6.
    Ishibashi H, Takagaki K, Imada N, Ikeda M (1994) First total synthesis of the benzopyranobenzazepine alkaloid (±)-Clavizepine. Synlett 149–150. doi:10.1055/s-1994-22734
  7. 7.
    Knight DW, Little PB (1998) The First high-yielding benzyne cyclisation using a phenolic nucleophile: a new route to xanthenes. Synlett 1141–1143. doi:10.1055/s-1998-1878
  8. 8.
    Jha A, Beal J (2004) Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone. Tetrahedron Lett 45: 8999–9001. doi:10.1016/j.tetlet.2004.10.046 CrossRefGoogle Scholar
  9. 9.
    Kuo CW, Fang JM (2001) synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl-carbonyl coupling reactions. Synth Commun 31: 877–892. doi:10.1081/SCC-100103323 CrossRefGoogle Scholar
  10. 10.
    Das B, Laxminarayana K, Krishnaiah M, Srinivas Y (2007) An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives. Synlett 3107–3112. doi:10.1055/s-2007-990922
  11. 11.
    Sing PR, Singh DU, Samant SD (2004) Sulphamic acid—an efficient and cost-effective solid acid catalyst for the Pechmann reaction. Synlett 1909–1912. doi:10.1055/s-2004-830858
  12. 12.
    Heravi MM, Nami N, Oskooie HA, Hekmatshoar R (2006) One-pot synthesis of some nitrogen and sulfur heterocycles using thiosemicarbazide under microwave irradiation in a solventless system. Phosphorus Sulfur Silicon 181: 87–91. doi:10.1080/104265090968992 CrossRefGoogle Scholar
  13. 13.
    Heravi MM, Bakhtiari Kh, Bamoharram FF (2006) An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdophosphoric acid. Catal Commun 7: 499–501. doi:10.1016/j.catcom.2006.01.003 CrossRefGoogle Scholar
  14. 14.
    Heravi MM, Bakhtiari Kh, Bamoharram FF (2006) 12-Molybdophosphoric acid: a recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones. Catal Commun 7: 373–376. doi:10.1016/j.catcom.2005.12.007 CrossRefGoogle Scholar
  15. 15.
    Heravi MM, Derikvand F, Bamoharram FF (2005) A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin-2(1H)-one using 12-tungstophosphoric acid. J Mol Catal A 242: 173–175. doi:10.1016/j.molcata.2005.08.009 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  1. 1.Department of Chemistry, School of SciencesAzzahra UniversityTehranIran

Personalised recommendations