Radical cascade cyclizations and platinum(II)-catalyzed cycloisomerizations of ynamides |
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Authors: | Fré dé ric Marion,Louis Fensterbank,Max Malacria |
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Affiliation: | Université Pierre et Marie Curie, Laboratoire de Chimie Organique, associé au CNRS, Institut de Chimie Moléculaire FR2769, 04 place Jussieu, Tour 44-54 2ème étage, B229, 75252 Paris Cedex 05, France |
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Abstract: | Ynamides are tested as new partners in radical and organometallic transformations. A radical cascade involving a 5-exo-dig cyclization followed by a 6-endo-trig radical trapping transforms ynamides into hetero-polycyclic compounds such as isoindoles, isoindolinones and pyrido-isoindolones. Various ene-tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This unprecedented and easily operated process can be coupled with a hydrolysis of the intermediate cyclic tosylenamides in a one-pot transformation, which provides cyclobutanones. |
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Keywords: | Cycloisomerization Heterocycles Platinum Radical Cascades Radical cyclization (Tosyl)-ynamides |
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