Journal
TETRAHEDRON
Volume 62, Issue 48, Pages 11100-11105Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.09.031
Keywords
hypervalent iodine; N-acylnitrenium; indazolone; pyrazolone
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The synthesis of new indazolone and pyrazolone derivatives starting from methyl anthranilate type substrates is presented. This general approach constitutes a novel and advantageous alternative for the synthesis of the target heterocycles, which implies the use of the environmentally friendly oxidizer PIFA. The synthetic design includes the oxidation of N-arylamides by the hypervalent iodine reagent to the corresponding N-acylnitrenium ions, which can be intramolecularly trapped by an amine moiety to furnish the title compounds by formation of a new N-N single bond. (c) 2006 Elsevier Ltd. All rights reserved.
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