Monatshefte für Chemie - Chemical Monthly

, Volume 145, Issue 8, pp 1353–1356 | Cite as

One-pot and solvent-free synthesis of aliphatic and aromatic 1H-indazolo[2,1-b]phthalazinetriones catalyzed by boron sulfonic acid

Original Paper

Abstract

An efficient and simple method for the synthesis of aliphatic and aromatic 1H-indazolo[2,1-b]phthalazinetrione derivatives through a one-pot three-component condensation of phthalhydrazide, aldehyde, and dimedone in the presence of boron sulfonic acid as a reusable and efficient catalyst under solvent-free conditions is described. The reusability of catalyst, good to excellent yields, short reaction times, and the avoidance of harsh reagents are the main advantages of this method.

Graphical Abstract

Keywords

Boron sulfonic acid 1H-Indazolo[2,1-b]phthalazinetrione Multicomponent reactions Solvent-free 

Notes

Acknowledgments

The authors gratefully acknowledge the Payame Noor University (PNU) of Ilam for partial support of this work.

Supplementary material

706_2014_1194_MOESM1_ESM.doc (49 kb)
Supplementary material 1 (DOC 49 kb)

References

  1. 1.
    Zhu J, Bienaymé H (2005) Multicomponent reactions. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  2. 2.
    Dömling A (2006) Chem Rev 106:17CrossRefGoogle Scholar
  3. 3.
    Dömling A, Ugi I (2000) Angew Chem Int Ed 39:3169CrossRefGoogle Scholar
  4. 4.
    Ramón DJ, Yus M (2005) Angew Chem Int Ed 44:1602CrossRefGoogle Scholar
  5. 5.
    Ma C, Yang Y (2005) Org Lett 7:1343CrossRefGoogle Scholar
  6. 6.
    Cheng Y, Meth-Cohn O (2004) Chem Rev 104:2507CrossRefGoogle Scholar
  7. 7.
    Ruijter E, Scheffelaar R, Orru RVA (2011) Angew Chem Int Ed 50:6234CrossRefGoogle Scholar
  8. 8.
    Franklin EC (1935) Chem Rev 16:305CrossRefGoogle Scholar
  9. 9.
    Bergstrom FW (1944) Chem Rev 35:77CrossRefGoogle Scholar
  10. 10.
    Lichtenthaler FW (2002) Acc Chem Res 35:728CrossRefGoogle Scholar
  11. 11.
    Litvinov VP (2003) Russ Chem Rev 72:69CrossRefGoogle Scholar
  12. 12.
    Al-Assar F, Zelenin KN, Lesiovskaya EE, Bezhan IP, Chahchir BA (2002) Pharm Chem J 36:598CrossRefGoogle Scholar
  13. 13.
    Jain RP, Vederas JC (2004) Bioorg Med Chem Lett 14:3655CrossRefGoogle Scholar
  14. 14.
    Carling RW, Moore KW, Street LJ, Wild D, Isted C, Lesson PD, Thomas S, O’Cooner D, Mckernan RM, Quirk K, Cook SM, Atach JR, Waftord KA, Thompson SA, Dawson GR, Ferris P, Castro JL (2004) J Med Chem 47:1807CrossRefGoogle Scholar
  15. 15.
    Watanabe N, Kabasawa Y, Takase Y, Matsukura M, Miyazaki K, Ishihara H, Kodama K, Adachi H (1998) J Med Chem 41:3367CrossRefGoogle Scholar
  16. 16.
    Nomoto Y, Obase H, Takai H, Teranishi M, Nakamura J, Kubo K (1990) Chem Pharm Bull 38:2179CrossRefGoogle Scholar
  17. 17.
    El-Sakka SS, Soliman AH, Imam AM (2009) Afinidad 66:167Google Scholar
  18. 18.
    Zhang L, Guan LP, Sun XY, Wei CX, Chai KY, Quan ZS (2009) Chem Bio Drug Des 73:313CrossRefGoogle Scholar
  19. 19.
    Sinkkonen J, Ovcharenko V, Zelenin KN, Bezhan IP, Chakchir BA, Al-Assar F, Pihlaja K (2002) Eur J Org Chem 2002:2046CrossRefGoogle Scholar
  20. 20.
    Ryu CK, Park RE, Ma MY, Nho JH (2007) Bioorg Med Chem Lett 17:2577CrossRefGoogle Scholar
  21. 21.
    Li J, Zhao YF, Yuan XY, Xu JX, Gong P (2006) Molecules 11:574CrossRefGoogle Scholar
  22. 22.
    Sayyafi M, Seyyedhamzeh M, Khavasi HR, Bazgir A (2008) Tetrahedron 64:2375CrossRefGoogle Scholar
  23. 23.
    Shaterian HR, Ghashang M, Feyzi M (2008) Appl Catal A 345:128CrossRefGoogle Scholar
  24. 24.
    Khurana JM, Magoo D (2009) Tetrahedron Lett 50:7300CrossRefGoogle Scholar
  25. 25.
    Shaterian HR, Hosseinian A, Ghashang M (2009) Arkivoc 59Google Scholar
  26. 26.
    Shaterian HR, Khorami F, Amirzadeh A, Doostmohammadi R, Ghashang M (2009) J Iran Chem Res 2:57Google Scholar
  27. 27.
    Wang HJ, Zhang XN, Zhang ZH (2010) Monatsh Chem 141:425CrossRefGoogle Scholar
  28. 28.
    Ghorbani-Vaghei R, Karimi-Nami R, Toghraei-Semiromi Z, Amiri M, Ghavidel M (2011) Tetrahedron 67:1930CrossRefGoogle Scholar
  29. 29.
    Hasaninejad A, Zare A, Shekouhy M (2011) Tetrahedron 67:390CrossRefGoogle Scholar
  30. 30.
    Wang X, Ma W, Wu L, Yan FL (2010) J Chin Chem Soc 57:1341Google Scholar
  31. 31.
    Hamidian H, Fozooni S, Hassankhani A, Mohammadi SZ (2011) Molecules 16:9041CrossRefGoogle Scholar
  32. 32.
    Kiasat AR, Mouradzadegun A, Saghanezhad SJ (2013) J Serb Chem Soc 78:469CrossRefGoogle Scholar
  33. 33.
    Salehi P, Zolfigol MA, Shirini F, Baghbanzadeh M (2006) Curr Org Chem 10:2171CrossRefGoogle Scholar
  34. 34.
    Salehi P, Zolfigol MA, Fard MA (2004) J Braz Chem Soc 15:773CrossRefGoogle Scholar
  35. 35.
    Kiasat AR, Fallah-Mehrjardi M (2008) J Braz Chem Soc 19:1595CrossRefGoogle Scholar
  36. 36.
    Sajjadifar S, Mirshokraie SA, Javaherneshan N, Louie O (2012) Am J Org Chem 2:1CrossRefGoogle Scholar
  37. 37.
    Sajjadifar S (2013) Int J ChemTech Res 5:385Google Scholar
  38. 38.
    Sajjadifar S, Khosravani E, Shiri S (2013) Int J ChemTech Res 5:1969Google Scholar
  39. 39.
    Sajjadifar S, Rezayati S (2013) Int J ChemTech Res 5:1964Google Scholar
  40. 40.
    Zolfigol MA, Khazaei A, Vahedi H, Mokhlesi M, Sajadifar S, Pirveysian M (2012) Phosphorus Sulfur Silicon Relat Elem 187:295CrossRefGoogle Scholar
  41. 41.
    Zolfigol MA, Vahedi H, Massoudi AH, Sajjadifar S, Loui O, Javaherneshan N (2011) Clin Biochem 44:219CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  1. 1.School of Chemistry, College of ScienceUniversity of TehranTehranIran
  2. 2.Department of ChemistryPayame Noor UniversityTehranIran

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