%0 Journal Article
%A Correa, Arkaitz
%A Tellitu, Imanol
%A Domínguez, Esther
%A SanMartin, Raul
%D 2006
%T Novel Alternative for the N−N Bond Formation through a
PIFA-Mediated Oxidative Cyclization and Its Application to the
Synthesis of Indazol-3-ones†
%U 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_/3372283
%R 10.1021/jo060070+.s001
%2 https://ndownloader.figshare.com/files/5215744
%K approach features
%K series
%K Cyclization
%K Application
%K intramolecular
%K cyclization step
%K methyl anthranilates
%K access
%K Formation
%K Oxidative
%K synthesis
%K amine moiety
%K heterocycle
%K hypervalent iodine reagent PIFA
%K formation
%K acylnitrenium
%K target N
%K Bond
%K disubstituted indazolone derivatives
%K Indazol
%K Synthesi
%K bond
%X The synthesis of a series of N,N‘-disubstituted indazolone derivatives starting from methyl anthranilates
is presented. This general approach features a novel and easy way for access to the target N-heterocycles
by formation of a new N−N single bond. The key cyclization step embraces the formation of an
N-acylnitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its succeeding
intramolecular trapping by the amine moiety under rather mild experimental conditions.
%I ACS Publications