Chemoselective Aromatic Azido Reduction with Concomitant Aliphatic Azide Employing Al/Gd Triflates/NaI and ESI‐MS Mechanistic Studies |
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| Authors: | Ahmed Kamal Dr Nagula Markandeya Nagula Shankaraiah Dr C?Ratna Reddy S Prabhakar C?Sanjeeva Reddy Prof Marcos?N Eberlin Prof Leonardo Silva?Santos Prof |
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| Institution: | 1. Chemical Biology Laboratory, Indian Institute of Chemical Technology, Hyderabad 500 007 (India), Fax: (+91)?40‐27193189;2. Department of Chemistry, Kakatiya University, Warangal 506 009, A.P. (India), Fax: (+91)870‐2439600;3. ThoMSon Mass Spectrometry Laboratory, University of Campinas, Unicamp (Brazil);4. Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Talca University, Talca, P.O. Box 747 (Chile) |
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| Abstract: | 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 pyrrolo2,1‐c]1,4]benzodiazepines, and fused2,1‐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. |
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| Keywords: | amines azides cyclization heterocycles mass spectrometry reduction |
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