Synthesis of (Z)-N-Alkenylazoles and Pyrroloisoquinolines from α-N-Azoleketones through Pd-Catalyzed Tosylhydrazone Cross-Couplings

Authors

  • Lucía Florentino,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, c/Julián Clavería 8. Oviedo. 33006 (Spain), Fax: (+34) 985-103446
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  • Prof. Dr. Fernando Aznar,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, c/Julián Clavería 8. Oviedo. 33006 (Spain), Fax: (+34) 985-103446
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  • Dr. Carlos Valdés

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, c/Julián Clavería 8. Oviedo. 33006 (Spain), Fax: (+34) 985-103446
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, c/Julián Clavería 8. Oviedo. 33006 (Spain), Fax: (+34) 985-103446
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Abstract

original image

Azoles reacting in tandem: The ortho-stereodirecting effect is the key to the stereoselective synthesis of (Z)-N-alkenylazoles I through the tosylhydrazide-mediated Pd-catalyzed cross-coupling reaction of α-N-azoleacetophenones with ortho-substituted aryl halides and nonaflates (see scheme). Additionally, the preorganization of the alkene allowed for the development of an auto-tandem reaction involving an intramolecular C[BOND]H arylation leading to pyrroloisoquinolines II.

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