Journal
TETRAHEDRON
Volume 62, Issue 16, Pages 3856-3871Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.11.092
Keywords
cycloisomerization; heterocycles; platinum; radical cascades; radical cyclization; (tosyl)-ynamides
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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-isoindol ones. 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. (c) 2006 Elsevier Ltd. All rights reserved.
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