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Type: Artigo de periódico
Title: Chemoselective Aromatic Azido Reduction With Concomitant Aliphatic Azide Employing Al/gd Triflates/nal And Esi-ms Mechanistic Studies
Author: Kamal A.
Markandeya N.
Shankaraiah N.
Ratna Reddy C.
Prabhakar S.
Sanjeeva Reddy C.
Eberlin M.N.
Santos L.S.
Abstract: Aluminium and gadolinium inflates catalyze the chemoselective reduction of aromatic azides to the corresponding amines in combination with sodium iodide. This mild chemoselective method has been applied to the synthesis of various aryl amines, C2azido-substituted pyrrolo[2,1-c]-[1,4]benzodiazepines, and fused[2,1b]quinazolinones by an intramolecular azido reduction tandem cyclization reaction. Interestingly, this methodology selectively reduces aryl azides with enhanced yields and proceeds in shorter reaction times than previous strategies. The mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Rights: fechado
Identifier DOI: 10.1002/chem.200900853
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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