Skip to main content
SpringerLink
Log in

An efficient and convenient protocol for the synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An efficient and direct procedure for the synthesis of novel spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives is described. The process employs a condensation reaction of 2-aminobenzamides and isatins in the presence of a catalytic amount of KAl(SO4)2.12H2O (alum) in ethanol under reflux.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. Hour M, Huang L, Kuo S, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K (2000) J Med Chem 43:4479

    Article  CAS  Google Scholar 

  2. Misra VS, Saxena VK, Srivastava R (1983) Indian J Pharm Sci 45:207

    CAS  Google Scholar 

  3. Kacker IK, Zaheer SH (1951) J Indian Chem Soc 28:344

    CAS  Google Scholar 

  4. Gupta RC, Nath R, Shanker K, Bhargava KP, Kishore K (1979) J Indian Chem Soc 56:219

    CAS  Google Scholar 

  5. Parmar SS, Kumar R, Arora RC (1969) Indian J Med Res 57:245

    CAS  Google Scholar 

  6. Abdel JRJ, Volter W, Saeed M (2004) Tetrahedron Lett 45:3475

    Article  CAS  Google Scholar 

  7. Corbett JW, Ko SS, Rodgers JD, Gearhart LA, Magnus NA, Bachheler LT, Diamond S, Jeffey S, Trainor GL, Anderson PS, Erickson VK (2000) J Med Chem 43:2019

    Article  CAS  Google Scholar 

  8. Liu JF, Lee J, Dalton AM, Bi G, Yu L, Baldino CM, McElory E, Brown M (2005) Tetrahedron Lett 46:1241

    Article  CAS  Google Scholar 

  9. Moore JA, Sutherland GJ, Sowerby R, Kelly EG, Palermo S, Webster W (1969) J Org Chem 34:887

    Article  CAS  Google Scholar 

  10. Su W, Yang B (2002) Aust J Chem 55:695

    Article  CAS  Google Scholar 

  11. Shi D, Rong L, Wang J, Zhuang Q, Wang X, Hu H (2003) Tetrahedron Lett 44:3199

    Article  CAS  Google Scholar 

  12. Sadanandam YS, Reddy KRM, Rao AB (1987) Eur J Org Chem 22:169

    CAS  Google Scholar 

  13. Reo VB, Ratnam CV (1979) Indian J Chem 18B:409

    Google Scholar 

  14. Popp FD (1984) J Heterocycl Chem 21:1367

    Article  Google Scholar 

  15. Garrido F, Ibanez J, Gonalons E, Giraldez A (1975) Eur J Med Chem 10:143

    CAS  Google Scholar 

  16. Kamano Y, Zhang HP, Ichihara Y, Kizu H, Komiyama K, Itokawa H, Pettit GR (1995) Tetrahedron Lett 36:2783

    Article  CAS  Google Scholar 

  17. Jnaneshwarand GK, Deshpande VH (1999) J Chem Res S 632

  18. Klumpp DA, Yeung KY, Prakash GKS, Olah GA (1998) J Org Chem 63:4481

    Article  CAS  Google Scholar 

  19. Franklin DP (1973) Ger Patent 2,258,505

  20. Jursic B, Stevens ED (2002) Tetrahedron Lett 43:5681

    Article  CAS  Google Scholar 

  21. Chen C, Li X, Neumann CS, Lo MMC, Schreiber SL (2005) Angew Chem Int Ed 44:2249

    Article  CAS  Google Scholar 

  22. Alcaide B, Almendros P, Acebes RR (2006) J Org Chem 71:2346

    Article  CAS  Google Scholar 

  23. Dabiri M, Salehi P, Otokesh S, Bahramnejad M, Kozehgiry Gh, Mohammadi AA (2005) Tetrahedron Lett 46:6123

    Article  CAS  Google Scholar 

  24. Azizian J, Mohammadi AA, Karimi N, Karimi AR, Mohammadizadeh MR (2006) Catal Commun 7:752

    Article  CAS  Google Scholar 

  25. Azizian J, Mohammadi AA, Karimi AR, Mohammadizadeh MR (2005) J Org Chem 70:350

    Article  CAS  Google Scholar 

  26. Dabiri M, Salehi P, Bagebanzadeh M, Bahramnejad M (2007) Monatsh Chem 138:1253

    Article  CAS  Google Scholar 

  27. Dabiri M, Bagebanzadeh M, Kiani SH, Vakilzadeh Y (2007) Monatsh Chem 138:997

    Article  CAS  Google Scholar 

  28. Mohammadi AA, Azizian J, Hadadzahmatkesh A, Asghariganjeh MR (2008) Heterocycles 75:947

    Article  CAS  Google Scholar 

  29. Dabiria M, Salehib P, Mohammadia AA, Baghbanzadeha M, Kozehgiry Gh (2004) J Chem Res S 570

  30. Clark RH, Wagner EC (1944) J Org Chem 9:55

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support from the Research Council of Shahid Beheshti University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Shahid Beheshti University, P.O. Box 19395-4716, Tehran, Iran

    M. Dabiri, Ali A. Mohammadi & Hassan Qaraat

Authors
  1. M. Dabiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ali A. Mohammadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hassan Qaraat
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to M. Dabiri or Ali A. Mohammadi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dabiri, M., Mohammadi, A.A. & Qaraat, H. An efficient and convenient protocol for the synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives. Monatsh Chem 140, 401–404 (2009). https://doi.org/10.1007/s00706-008-0040-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0040-3

Keywords

Search

Navigation