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Chemoselective Aromatic Azido Reduction with Concomitant Aliphatic Azide Employing Al/Gd Triflates/NaI and ESI‐MS Mechanistic Studies
Author(s) -
Kamal Ahmed,
Markandeya Nagula,
Shankaraiah Nagula,
Reddy C. Ratna,
Prabhakar S.,
Reddy C. Sanjeeva,
Eberlin Marcos N.,
Silva Santos Leonardo
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900853
Subject(s) - chemistry , azide , aryl , sodium azide , chemoselectivity , iodide , intramolecular force , combinatorial chemistry , tandem , cascade reaction , medicinal chemistry , organic chemistry , catalysis , alkyl , materials science , composite material
Aluminium and gadolinium triflates 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, C2‐azido‐substituted pyrrolo[2,1‐ c ][1,4]benzodiazepines, and fused[2,1‐ b ]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.