Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 7, pp 743–748 | Cite as

Contributions to syntheses of pyrrolo[2,1-a]phthalazines

  • Mino R. Caira
  • Emilian Georgescu
  • Florentina Georgescu
  • Florin Albota
  • Florea Dumitrascu
Original Paper
First Online:
Received:
Accepted:

Abstract

Structural elucidation of the dihydro derivatives obtained as by-products in the classic salt method synthesis of pyrrolo[2,1-a]phthalazines and acetylenic dipolarophiles was achieved by X-ray diffraction analysis of a representative compound. In addition, new pyrrolo[2,1-a]phthalazines were obtained by a one-pot three-component reaction that avoids the formation of the dihydro derivative intermediates.

Graphical abstract

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Keywords

Pyrrolo[2,1-a]phthalazine X-ray structure determination N-ylides One-pot three-component reaction 
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Notes

Acknowledgments

M.R.C. thanks the University of Cape Town and the National Research Foundation for research support.

References

  1. 1.
    Dorweiler C, Holderbaum M, Munzmay T, Spang P, Durr H, Kruger C, Raabe E (1988) Chem Ber 121:843CrossRefGoogle Scholar
  2. 2.
    Cheng Y, Ma B, Wudl F (1999) J Mater Chem 9:2183CrossRefGoogle Scholar
  3. 3.
    Mitsumori T, Bendikov M, Sedó J, Wudl F (2003) Chem Mater 15:3759CrossRefGoogle Scholar
  4. 4.
    Uff BC, Ghaem-Maghami G, Budhram RS, Wilson CL, Apatu JO (1989) J Heterocycl Chem 26:571CrossRefGoogle Scholar
  5. 5.
    Galin FZ, Sakhautdinov IM, Tukhavatullin OR (2007) Russ Chem Bull Int Ed 53:2305CrossRefGoogle Scholar
  6. 6.
    Siriwardana AI, Nakamura I, Yamamoto Y (2004) J Org Chem 69:3202CrossRefGoogle Scholar
  7. 7.
    Komatsu M, Kasano Y, Yamaoka S, Minakata S (2003) Synthesis 35(9):1398Google Scholar
  8. 8.
    Bridge AW, Hursthouse MB, Lehmann CW, Lythgoe DJ, Newton CG (1993) J Chem Soc Perkin Trans 1:1839CrossRefGoogle Scholar
  9. 9.
    Potts KT, Bordeaux KG, Kuehnling WR, Salsbury RL (1985) J Org Chem 50:1677CrossRefGoogle Scholar
  10. 10.
    Zugrăvescu I, Petrovanu M (1976) N-Ylid chemistry. McGraw-Hill, New York, p 239Google Scholar
  11. 11.
    Khlebnikov AF, Kostik EI, Kostikov RR (1993) Synthesis 25(6):568Google Scholar
  12. 12.
    Zhou J, Hu Y, Hu H (2000) J Heterocycl Chem 37:1165CrossRefGoogle Scholar
  13. 13.
    Butnariu RM, Caprosu MD, Bejan V, Ungureanu M, Poiata A, Tuchilus C, Florescu M, Mangalagiu I (2007) J Heterocycl Chem 44:1CrossRefGoogle Scholar
  14. 14.
    Caprosu MC, Zbancioc GN, Moldoveanu CC, Mangalagiu I (2004) Collect Czech Chem Commun 69:426CrossRefGoogle Scholar
  15. 15.
    Dumitrascu F, Mitan CI, Draghici C, Caproiu MT, Raileanu D (2001) Tetrahedron Lett 42:8379CrossRefGoogle Scholar
  16. 16.
    Dumitrascu F, Draghici C, Caproiu MT, Dumitrescu D, Badoiu A (2006) Rev Roum Chim 51:643Google Scholar
  17. 17.
    Dumitrascu F, Caira MR, Draghici C, Caproiu MT, Barbu L (2009) Rev Chim (Bucharest) 60:851Google Scholar
  18. 18.
    Sharp JT, Wilson P, Parsons S, Gould RO (2000) J Chem Soc Perkin Trans 1:1139CrossRefGoogle Scholar
  19. 19.
    Dömling A (2006) Chem Rev 106:17CrossRefGoogle Scholar
  20. 20.
    Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  21. 21.
    Maisonneuve S, Xie J (2009) Synlett 20(18):2977Google Scholar
  22. 22.
    Reddy Udagandla C, Saikia Anil K (2010) Synlett 21(7):1027Google Scholar
  23. 23.
    Ranjabar-Karimi R, Beiki-Shoraki K, Amiri A (2010) Monatsh Chem 141:1101CrossRefGoogle Scholar
  24. 24.
    Keri RS, Hosamani KM (2010) Monatsh Chem 141:883CrossRefGoogle Scholar
  25. 25.
    Gladkov ES, Sirko SN, Shishkina SV, Shishkin OV, Knyazeva IV, Desenko SM, Chebanov VA (2010) Monatsh Chem 141:773CrossRefGoogle Scholar
  26. 26.
    Wang HJ, Zhang XN, Zhang ZH (2010) Monatsh Chem 141:425CrossRefGoogle Scholar
  27. 27.
    Yavari I, Sayyed-Alangy SZ, Hajinasiri R, Sajjadi-Ghotbabadi H (2009) Monatsh Chem 140:209CrossRefGoogle Scholar
  28. 28.
    Dumitrascu F, Draghici C, Caproiu MT, Dumitrescu DG, Popa MM (2009) Rev Roum Chim 53:923Google Scholar
  29. 29.
    Georgescu E, Caira MR, Georgescu F, Draghici B, Popa MM, Dumitrascu F (2009) Synlett 20(11):1795Google Scholar
  30. 30.
    Caira MR, Georgescu E, Georgescu F, Draghici B, Popa MM, Dumitrascu F (2009) Arkivoc xii:242Google Scholar
  31. 31.
    Dumitrascu F, Caproiu MT, Georgescu F, Draghici B, Popa MM, Georgescu E (2010) Synlett 21(16):2407Google Scholar
  32. 32.
    Dumitrascu F, Georgescu E, Caira MR, Georgescu F, Popa MM, Draghici B, Dumitrescu DG (2009) Synlett 20(20):3336Google Scholar
  33. 33.
    Georgescu E, Dumitrascu F, Georgescu F, Draghici C, Popa MM (2010) Rev Roum Chim 55:217Google Scholar
  34. 34.
    Hooft R (1988) V. Collect: Data Collection Software, Nonius BV, Delft, The NetherlandsGoogle Scholar
  35. 35.
    Otwinowski Z, Minor W (1997) Methods Enzymol 276:307CrossRefGoogle Scholar
  36. 36.
    Sheldrick GM (2008) Acta Cryst A64:112Google Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Mino R. Caira
    • 1
  • Emilian Georgescu
    • 2
  • Florentina Georgescu
    • 2
  • Florin Albota
    • 3
  • Florea Dumitrascu
    • 3
  1. 1.Department of ChemistryUniversity of Cape TownRondeboschSouth Africa
  2. 2.Oltchim Research CenterRamnicu ValceaRomania
  3. 3.Centre of Organic Chemistry “C. D. Nenitzescu”Roumanian AcademyBucharestRomania

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