An Efficient One-pot Synthesis of 4H-Pyrrolo[3,2,1-ij]quinolines

Summary.

Dialkyl 4H-pyrrolo[3,2,1-ij]quinoline-4,5-dicarboxylates are obtained in quantitative yields from the 1:1:1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylates, and indole-7-carboxaldehyde.

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References

  1. JF Swinbourne HJ Hunt G Klinkert (1987) Adv Heterocycl Chem 23 103

    Google Scholar 

  2. Astill BD, Boekelheide V (1958) J Org Chem 23: 316; Hallas G, Taylor DC (1964) J Chem Soc 1518

  3. D Paris M Cottin P Demonchaux G Augert P Dupassieux P Lenoir MJ Peck D Jasserand (1995) J Med Chem 38 669 Occurrence Handle10.1021/jm00004a013 Occurrence Handle1:CAS:528:DyaK2MXjsFaisLY%3D

    Article  CAS  Google Scholar 

  4. M Isaac A Slassi A O’Brien L Edwards N MacLean D Bueschkens DKH Lee K McCallum IDe Lannoy L Demchyshyn R Kamboj (2000) Bioorg Med Chem Lett 10 919 Occurrence Handle1:CAS:528:DC%2BD3cXjvVSjtLc%3D

    CAS  Google Scholar 

  5. K Tsuji H Tsubouchi H Ishikawa (1995) Chem Pharm Bull 43 1678 Occurrence Handle1:CAS:528:DyaK2MXpsF2nsLc%3D

    CAS  Google Scholar 

  6. I van Wijngaarden D Hamminga R van Hes P Standaar J Tipker M Tulip F Mol B Oliver AI de Jonge (1993) J Med Chem 36 3693 Occurrence Handle10.1021/jm00075a026 Occurrence Handle1:CAS:528:DyaK2cXhtlCgtLk%3D

    Article  CAS  Google Scholar 

  7. KC Majumdar SK Chattopadhyay AT Khan (1989) J Chem Soc Perkin Trans 1 1285

    Google Scholar 

  8. Goldstein S, Dambek P (1989) Synthesis 221

  9. AE Steck TL Fletcher (1974) J Heterocycl Chem 11 387 Occurrence Handle1:CAS:528:DyaE2cXlt1Sns7Y%3D

    CAS  Google Scholar 

  10. Adib M, Mollahosseini M, Yavari H, Sayahi MH, Bijanzadeh HR (2004) Synlett 1086

  11. M Adib K Ghanbary M Mostofi HR Bijanzadeh (2005) Tetrahedron 61 2645 Occurrence Handle1:CAS:528:DC%2BD2MXhs1aht7g%3D

    CAS  Google Scholar 

  12. I Yavari M Adib (2001) Tetrahedron 57 5873 Occurrence Handle1:CAS:528:DC%2BD3MXltVahsLo%3D

    CAS  Google Scholar 

  13. I Yavari M Adib M Esnaashari (2001) Monatsh Chem 132 1557 Occurrence Handle1:CAS:528:DC%2BD38XhsVSmtrc%3D

    CAS  Google Scholar 

  14. I Yavari M Adib F Jahani-Moghaddam (2002) Monatsh Chem 133 1431 Occurrence Handle1:CAS:528:DC%2BD38Xns12gs7Y%3D

    CAS  Google Scholar 

  15. I Yavari M Adib S Abdolmohammadi M Aghazadeh (2003) Monatsh Chem 134 1093 Occurrence Handle1:CAS:528:DC%2BD3sXlsFKmsLw%3D

    CAS  Google Scholar 

  16. Zbiral E (1974) Synthesis 775; Becker KB (1980) Tetrahedron 36: 1717; Ferrer P, Avendo C, Sollhubor M (1995) Liebigs Ann Chem 1895; Johnson AW (1996) Ylid Chemistry, Academic Press, New York; Kolodiazhynyi OI (1997) Russ Chem Rev 66: 225; Pietrusiewiz KM, Zablocka M (1983) Chem Rev 83: 109; Bestmann HJ, Vostrowsky O (1983) Top Curr Chem 109: 85; Bestmann HJ, Zimmermann R (1970) Top Curr Chem 20: 88

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Correspondence to Mehdi Adib.

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Adib, M., Sayahi, M. An Efficient One-pot Synthesis of 4H-Pyrrolo[3,2,1-ij]quinolines. Monatsh. Chem. 137, 207–211 (2006). https://doi.org/10.1007/s00706-005-0420-x

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  • Keywords. Indole-7-carboxaldehyde; Acetylenic esters; Intramolecular Wittig reaction; Triphenylphosphine; 4H-Pyrrolo[3,2,1-ij]quinolines.