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Coumarin substituted pyrrolo-fused heterocyclic systems by 1,3-dipolar cycloadditon reactions

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Abstract

A variety of new pyrrolo-fused heterocyclic systems bearing a 3-carbonylchromen-2-one moiety on the pyrrole rings was obtained based on 1,3-dipolar cycloaddition reactions of corresponding cycloimmonium-ylides, generated in situ from the quaternary salts of several N-heterocycles with 3-(2-bromoacetyl)-2H-chromen-2-one, with electron-deficient alkynes. The synthetic strategies were both one-pot, three-component and classical multistep 1,3-dipolar cycloaddition reactions. The all newly synthesized compounds were structurally characterized by elemental analysis, IR and NMR spectroscopy.

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Acknowledgments

MP gratefully acknowledges financial support of the Sectorial Operational Programme Human Resources Development 2007-2013 of the Ministry of European Funds through the Financial Agreement POSDRU/159/1.5/S/134398.

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Authors and Affiliations

  1. Center for Organic Chemistry C.D. Nenitzescu, Romanian Academy, Spl. Independentei 202B, 060023, Bucharest, Romania

    Marcel M. Popa, Constantin Draghici & Florea Dumitrascu

  2. Faculty of Applied Chemistry and Materials Science, ‘Politehnica’ University of Bucharest, Polizu Street 1-7, 011061, Bucharest, Romania

    Marcel M. Popa

  3. Research Center Oltchim, Str. Uzinei 1, 240050, Ramnicu Valcea, Romania

    Emilian Georgescu

  4. Research Department, Teso Spec SRL, Str. Muncii 53, 915200, Fundulea, Calarasi, Romania

    Florentina Georgescu

  5. Faculty of Pharmacy, “Ovidius” University, Aleea Universitatii nr.1, Campus Corp B, 900470, Constantza, Romania

    Denisa Dumitrescu

Authors
  1. Marcel M. Popa
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  2. Emilian Georgescu
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  3. Constantin Draghici
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  4. Florentina Georgescu
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  5. Florea Dumitrascu
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  6. Denisa Dumitrescu
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Corresponding author

Correspondence to Marcel M. Popa.

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Popa, M.M., Georgescu, E., Draghici, C. et al. Coumarin substituted pyrrolo-fused heterocyclic systems by 1,3-dipolar cycloadditon reactions. Monatsh Chem 146, 2029–2040 (2015). https://doi.org/10.1007/s00706-015-1563-z

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  • DOI: https://doi.org/10.1007/s00706-015-1563-z

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