Skip to main content
Log in

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
  • Published:
Molecular Diversity Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  Google Scholar 

  3. Menchen SM, Benson SC, Lam JYL, Zhen W, Sun D, Rosenblum BB, Khan SH, Taing M (2003) Sulfonated diarylrhodamine dyes. US Patent 6583168

  4. Sarma RJ, Baruah JB (2005) One step synthesis of dibenzoxanthenes. Dyes Pigment 64: 91–92. doi:10.1016/j.dyepig.2004.03.010

    Article  CAS  Google Scholar 

  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. 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. 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. 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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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. 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. 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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Majid M. Heravi or Khadijeh Bakhtiari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Heravi, M.M., Alinejhad, H., Bakhtiari, K. et al. 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. Mol Divers 14, 621–626 (2010). https://doi.org/10.1007/s11030-009-9196-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-009-9196-y

Keywords

Navigation