New synthetic route to N-arylated pyridazinones from aryldiazonium salts

Authors

  • Daniel Cassú Universitat de Girona. Institut de Química Computacional i Catàlisi (IQCC) Universitat de Girona. Departament de Química
  • Ouissam El Bakouri Universitat de Girona. Institut de Química Computacional i Catàlisi (IQCC) Universitat de Girona. Departament de Química
  • Miquel Solà Universitat de Girona. Institut de Química Computacional i Catàlisi (IQCC) Universitat de Girona. Departament de Química
  • Anna Pla-Quintana Universitat de Girona. Institut de Química Computacional i Catàlisi (IQCC) Universitat de Girona. Departament de Química
  • Anna Roglans Universitat de Girona. Institut de Química Computacional i Catàlisi (IQCC) Universitat de Girona. Departament de Química

Keywords:

N-arylated pyridazinones, aryldiazonium salts, DFT calculations.

Abstract

Pyridazinones are organic compounds that are commonly found in drugs, pesticides, and natural products with biological activity. To date, a considerable number of synthetic routes to obtain pyridazinones have been published although only a few have described efficient pathways to prepare N-arylated pyridazinones. In contrast to methods found in literature in which strong reaction conditions or metallic catalysts are employed, this study proposes a new route to obtain N-arylated pyridazinones using aryldiazonium salts and furan derivatives in mild reaction conditions with water as the solvent. Diazonium salts are highly reactive compounds and so their use results in an important gain in terms of the efficiency of the process. The reaction mechanism is elucidated by DFT calculations and confirmed by empirical tests.

Keywords: N-arylated pyridazinones, aryldiazonium salts, DFT calculations.

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Author Biography

Daniel Cassú, Universitat de Girona. Institut de Química Computacional i Catàlisi (IQCC) Universitat de Girona. Departament de Química



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