10.1021/jo060070+.s002
Arkaitz Correa
Arkaitz
Correa
Imanol Tellitu
Imanol
Tellitu
Esther Domínguez
Esther
Domínguez
Raul SanMartin
Raul
SanMartin
Novel Alternative for the N<i>−</i>N Bond Formation through a
PIFA-Mediated Oxidative Cyclization and Its Application to the
Synthesis of Indazol-3-ones<sup>†</sup>
American Chemical Society
2006
approach features
series
Cyclization
Application
intramolecular
cyclization step
methyl anthranilates
access
Formation
Oxidative
synthesis
amine moiety
heterocycle
hypervalent iodine reagent PIFA
formation
acylnitrenium
target N
Bond
disubstituted indazolone derivatives
Indazol
Synthesi
bond
2006-04-28 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Novel_Alternative_for_the_N_i_i_N_Bond_Formation_through_a_PIFA_Mediated_Oxidative_Cyclization_and_Its_Application_to_the_Synthesis_of_Indazol_3_ones_sup_sup_/3372289
The synthesis of a series of N,N<i>‘</i>-disubstituted indazolone derivatives starting from methyl anthranilates
is presented. This general approach features a novel and easy way for access to the target <i>N</i>-heterocycles
by formation of a new N<i>−</i>N single bond. The key cyclization step embraces the formation of an
<i>N</i>-acylnitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its succeeding
intramolecular trapping by the amine moiety under rather mild experimental conditions.