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A green approach to the amidation of heterocyclic bases: the use of sunlight and air

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Abstract

A easy and environmentally friendly method for the photochemical functionalisation of the heterocyclic bases is described. The selective introduction of the amido group of formamide, using sunlight and air in the presence of TiO2, has allowed to obtain the desired products in mild conditions with high conversions. The comparison of these results with those previously reported, in the presence of H2O2 instead of air, clarifies some aspects of the reaction mechanism.

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References

  1. A. Studer and M. Bossart, in Radicals in Organic Synthesis, Vol. II, P. Renauld and M. P. Sibi (Eds), p. 62, Wiley-VCH, New York, NY (2001).

    Chapter  Google Scholar 

  2. F. Minisci, Synthesis, 1 (1973).

  3. F. Minisci, Top. Curr. Chem. 62, 1 (1976).

    Article  CAS  Google Scholar 

  4. F. Minisci, E. Vismara and F. Fontana, Heterocycles 28, 489 (1989).

    Article  CAS  Google Scholar 

  5. F. Minisci, F. Fontana and E. Vismara, J. Heterocycl. Chem. 27, 79 (1990).

    Article  CAS  Google Scholar 

  6. O. Porta and F. Minisci, in Handbook of C−H Transformations Gerard Dyker (Ed.), p. 212. Wiley-VCH, New York, NY (2005).

    Google Scholar 

  7. M. A. Fox and M. T. Dulay, Chem. Rev. 93, 341 (1993).

    Article  CAS  Google Scholar 

  8. A. Maldotti, A. Molinari and R. Amadelli, Chem. Rev. 102, 3811 (2002).

    Article  CAS  Google Scholar 

  9. T. Del Giacco, M. Ranchella, C. Rol and G. V. Sebastiani, J. Phys. Org. Chem. 13, 745 (2000).

    Article  Google Scholar 

  10. M. Ranchella, C. Rol and G. V. Sebastiani, J. Chem. Res. (Suppl.), 239 (2002).

  11. T. Del Giacco, C. Rol and G. V. Sebastiani, J. Phys. Org. Chem. 16, 127 (2003).

    Article  Google Scholar 

  12. H. Keck, W. Schindler, F. Knock and H. Kisch, Chem. Eur. J. 3, 1638 (1997).

    Article  CAS  Google Scholar 

  13. H. Kisch, Adv. Photochem. 62, 93 (2001).

    Article  Google Scholar 

  14. T. Caronna, C. Gambarotti, L. Palmisano, C. Punta and F. Recupero, Chem. Commun., 2350 (2003).

  15. T. Caronna, C. Gambarotti, L. Palmisano, C. Punta and F. Recupero, J. Photochem. Photobiol. A: Chem. 171, 237 (2005).

    Article  CAS  Google Scholar 

  16. M. Schiavello, Heterogeneous Photocatalysis, Wiley, New York, NY (1995).

    Google Scholar 

  17. F. Minisci, E. Vismara, F. Fontana, G. Morini, M. Serravalle and C. Giordano, J. Org. Chem. 52, 730 (1987).

    Article  CAS  Google Scholar 

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Correspondence to Tullio Caronna.

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Caronna, T., Gambarotti, C., Mele, A. et al. A green approach to the amidation of heterocyclic bases: the use of sunlight and air. Res. Chem. Intermed. 33, 311–317 (2007). https://doi.org/10.1163/156856707779238603

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  • DOI: https://doi.org/10.1163/156856707779238603

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