Advertisement

Molecular Diversity

, Volume 12, Issue 3–4, pp 181–185 | Cite as

A three component one-pot procedure for the synthesis of [1,2,4]triazolo/benzimidazolo-quinazolinone derivatives in the presence of H6P2W18O62 · 18H2O as a green and reusable catalyst

  • Majid M. Heravi
  • Leila Ranjbar
  • Fatemeh Derikvand
  • Behnoush Alimadadi
  • Hossien A. Oskooie
  • Fatemeh F. Bamoharram
Short Communication

Abstract

A rapid and efficient one-pot method for the synthesis of quinazolinone derivatives and related heterocycles by condensation of 2-amino benzimidazole and 3-amino-1,2,4-triazole, as amine sources, with dimedone and different aldehydes in the presence of H6P2W18O62 · 18H2O as a green and reusable catalyst in refluxing acetonitrile has been developed.

Keywords

Quinazolinones 2-Aminobenzimidazole 3-Amino-1,2,4-triazole Heteropolyacids Reusable catalysts 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Weber L (2002) The application of multi-component reactions in drug discovery. Curr Med Chem 9: 2085–2093PubMedGoogle Scholar
  2. 2.
    Hulme C, Gore V (2003) Multi-component reactions: emerging chemistry in drug discovery from xylocain to crixivan. Curr Med Chem 10: 51–80PubMedCrossRefGoogle Scholar
  3. 3.
    Domling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3168–3210CrossRefGoogle Scholar
  4. 4.
    Alagarsamy V, Pathak US (2007) Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b] quinazolin-9-ones. Bioorg Med Chem 15: 3457–3462PubMedCrossRefGoogle Scholar
  5. 5.
    Alagarsamy V, Solomon VR, Murugan M (2007) Synthesis and pharmacological investigation of novel 4-benzyl-1-substituted-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones as new class of H1-antihistaminic agents. Bioorg Med Chem 15: 4009–4015PubMedCrossRefGoogle Scholar
  6. 6.
    Alagarsamy V (2004) Synthesis and pharmacological investigation of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones as histamine H1-receptor blockers. Pharmazie 59: 753–755PubMedGoogle Scholar
  7. 7.
    Alagarsamy V, Murugananthan G, Venkateshperumal R (2003) Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-methyl-3-substituted quinazolin-4-(3H)-ones. Biol Pharm Bull 26: 1711–1714PubMedCrossRefGoogle Scholar
  8. 8.
    Hour MJ, Huang LJ, Kuo SC, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee KH (2000) 6-Alkylamino- and 2,3-dihydro-3′-methoxy-2-phenyl-4-quinazolinones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. J Med Chem 43: 4479–4487PubMedCrossRefGoogle Scholar
  9. 9.
    Alagarsamy V, Revathi R, Meena S, Ramaseshu KV, Rajasekaran S, De Clercq E (2004) Anti HIV, antibacterial and antifungal activates of some 2,3- disubstituted quinazolin 4(3H) ones. Indian J Pharm Sci 66: 459–462Google Scholar
  10. 10.
    Liu KC, Hu MK (1986) Guanidine-annelated heterocycles, VII: synthesis and antihypertensive activity of 2,10-dimethyl-5H, 10H-1,2,4-triazolo[5,1-b]quinazolin-5-one. Arch Pharm 319: 188–189CrossRefGoogle Scholar
  11. 11.
    (a) Eicher T, Hauptmann S (1994) Chemie der Heterocyclen. Georg Thieme Verlag, Stuttgart, New York, p 398; (b) Gilchrist TL (1995) Heterocyclenchemie; Neunhoeffer H (ed); Wiley-VCH, New York, p 270; (c) Lehn JM (1995) supramolecular chemistry-concepts and perspectives. VCH, Weinheim, Chap 9; (d) Haridas V, Lal K, Sharma YK (2007) Design and synthesis of triazole-based peptide dendrimers. Tetrahedron Lett 48:4719–4722Google Scholar
  12. 12.
    Heravi MM, Derikvand F, Bamoharram FF (2007) Highly efficient, four-component one-pot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts. J Mol Catal A Chem 263: 112–114CrossRefGoogle Scholar
  13. 13.
    Heravi MM, Derikvand F, Ranjbar L, Bamoharram FF (2007) H14[NaP5W30O110] as a heterogeneous recyclable catalyst for the synthesis of 1,5-benzodiazepines. J Mol Catal A Chem 261: 156–159CrossRefGoogle Scholar
  14. 14.
    Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) H6P2W16O62: An efficient and reusable catalyst for one-pot synthesis of β-acetamido ketone and esters. Catal Commun 8: 289–291CrossRefGoogle Scholar
  15. 15.
    Heravi MM, Derikvand F, Ranjbar L, Oskooie HA, Bamoharram FF (2007) Catalytic oxidative cleavage of C=N bond in the presence of mixed-addenda vanadomolybdophosphate, H6PMo9V3O40 as a green and reusable catalyst. J Mol Catal A Chem 265: 186–188CrossRefGoogle Scholar
  16. 16.
    Komiyama T, Takaguchi Y, Tsuboi S (2004) Novel synthesis of 4-chloro-3-hydroxy-2-pyrone by the reaction of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester with magnesium chloride. Tetrahedron Lett 45: 6299–6031CrossRefGoogle Scholar
  17. 17.
    Evans DA, Tedrow JS, Shaw JT, Downey W (2002) Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. J Am Chem Soc 124: 392–393PubMedCrossRefGoogle Scholar
  18. 18.
    Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) A modified and green Dakin–West reaction: an efficient and convenient method for a one-pot synthesis of β-acetamido carbonyl compounds. J Mol Catal A Chem 271: 28–31CrossRefGoogle Scholar
  19. 19.
    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 Chem 242: 173–175CrossRefGoogle Scholar
  20. 20.
    (a) Mashraqui SH, Karnik MA (1998) Catalytic oxidation of Hantzsch 1,4-dihydropyridines by RuCl3 under oxygen atmosphere. Tetrahedron Lett 39:4895–4898; (b) Nakamichi N, Kawashita Y, Hayashi M (2002) Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid. Org Lett 4:3955-3957; (c) Nakamichi N, Kawashita Y, Hayashi M (2004) In the presence of activated carbon, Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines were aromatized with molecular oxygen to the corresponding pyridines and pyrazoles in excellent yields. Synthesis 1015–1020Google Scholar
  21. 21.
    Lipson VV, Desenko SM, Shirobokova MG, Borodina VV (2003) Synthesis of 9-aryl-6,6-dimethyl-5,6,7,9-tetrahydro-1,2,4-triazolo-[5,1-b]quinazolin-8(4H)ones. Chem Heterocycl Comp 39: 1213–1217CrossRefGoogle Scholar
  22. 22.
    Lipson VV, Desenko SM, Shishkina SV, Shirobokova MG, Shishkin OV, Orlov VD (2003) Cyclocondensation of 2-aminobenzimidazole with dimedone and its arylidene derivatives. Chem Heterocycl Comp 39: 1041–1047CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2008

Authors and Affiliations

  • Majid M. Heravi
    • 1
  • Leila Ranjbar
    • 1
  • Fatemeh Derikvand
    • 1
  • Behnoush Alimadadi
    • 1
  • Hossien A. Oskooie
    • 1
  • Fatemeh F. Bamoharram
    • 2
  1. 1.Department of Chemistry, School of SciencesAzzahra UniversityVanak, TehranIran
  2. 2.Department of ChemistryIslamic Azad University–Mashhad BranchMashhadIran

Personalised recommendations