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.

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.
T. Lanza; R. Leardini; M. Minozzi; D. Nanni; P. Spagnolo; G. Zanardi.
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/65465
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 4
  • Scopus 69
  • ???jsp.display-item.citation.isi??? 68
social impact