Tehran University of Medical Sciences

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Novel and Efficient Synthesis of Triazolobenzodiazepine Analogues Through the Sequential Ugi 4Cr-Click-N-Arylation Reactions Publisher



Asgari MS1 ; Soheilizad M2 ; Ranjbar PR1 ; Larijani B3 ; Rahimi R4 ; Mahdavi M3
Authors
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Authors Affiliations
  1. 1. School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
  2. 2. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  3. 3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Chemistry, Iran University of Science and Technology, Narmak, 16846-13114, Tehran, Iran

Source: Tetrahedron Letters Published:2019


Abstract

An efficient approach for the synthesis of N-alkyl-2-aryl-2-(6-oxo-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepin-5(6H)-yl)acetamides is described. The protocol involves Ugi four-component reaction of 2-bromobenzoic acid, propargylamine, aldehydes and isocyanides followed by in situ sequential click reaction of azide ion with triple bond and N-arylation reaction to afford desired products in good to excellent yields. © 2019 Elsevier Ltd