Cyclization of aryl radicals at the ipso-position of p-azido-substituted benzamides or 2-(phenyl)acetamides results in effective production of spirocyclohexadieniminyl radicals through prompt elimination of molecular nitrogen by transient azidocyclohexadienyl radicals. The outcoming iminyl radicals can be exploited in a new protocol for the synthesis of oxindoles or quinolones bearing spiro-cyclohexadienimine/-cyclohexadienone rings which are pivotal intermediates in the preparation of various biologically active indole compounds.
T. Lanza, R. Leardini, M. Minozzi, D. Nanni, P. Spagnolo, G. Zanardi. (2008). Approach to Spirocyclohexadienimines and Corresponding Dienones through Radical ipso Cyclization onto aromatic azides. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 47, 9439-9442 [10.1002/anie.200804333].
Approach to Spirocyclohexadienimines and Corresponding Dienones through Radical ipso Cyclization onto aromatic azides.
LANZA, TOMMASO;LEARDINI, RINO;MINOZZI, MATTEO;NANNI, DANIELE;SPAGNOLO, PIERO;ZANARDI, GIUSEPPE
2008
Abstract
Cyclization of aryl radicals at the ipso-position of p-azido-substituted benzamides or 2-(phenyl)acetamides results in effective production of spirocyclohexadieniminyl radicals through prompt elimination of molecular nitrogen by transient azidocyclohexadienyl radicals. The outcoming iminyl radicals can be exploited in a new protocol for the synthesis of oxindoles or quinolones bearing spiro-cyclohexadienimine/-cyclohexadienone rings which are pivotal intermediates in the preparation of various biologically active indole compounds.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.