Search

Abstract A gold-catalyzed intermolecular reaction of ynamides with 3-indolyl azides via the presumable α-imino gold carbenes has been developed, providing an alternative and efficient way for the synthesis of valuable 3-amino-β-carbolines in generally good to excellent yields. Importantly, this new protocol involves an unexpected 1,2-alkyl migration pathway. [ABSTRACT FROM AUTHOR]

[1,4]Oxazino[3,2- b ]indoles as well as 1 H -pyrazino[2,3- b ]indoles are constructed in good to excellent yields via gold-catalyzed cascade cyclization of (azido)ynamides. The use of readily available starting materials, a simple procedure and mild reaction conditions are other significant features of this method. [ABSTRACT FROM AUTHOR]

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. [Copyright &y& Elsevier]