Copper-Catalyzed Tandem Reactions of 2-Iodobenzamides with Sodium Azide: An Efficient Synthesis of [1,2,3]Triazolo[1,5-a][1,4]-benzodiazepin-6(5H)-ones

Abstract

Copper-catalyzed tandem reactions between 2-iodobenzamides with a propargyl group on the nitrogen atom moiety and sodium azide are presented, providing an efficient method for the synthesis of 3-substituted [1,2,3]triazolo [1,5-a][1,4]benzodiazepin-6(5H)-ones under mild conditions in moderate yields.

Facile one-pot synthesis of novel N-benzimidazolyl-α-arylnitrones catalyzed by salts of transition metals

“…1 The term is a contraction of the terms “nitrogen ketone”. 2,3 Nitrones have a 1,3-dipole structure; they are used in 1,3-dipolar cycloadditions 4 (especially for synthesis of oxaziridine, isoxazolines, oxadiazolidines, etc. 5 ) and formal cycloadditions in the synthesis of many natural products.…”

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

“…This synthetic protocol allows the preparation of a variety of selenium‐containing triazonines employing a wide range of arylyl(alk‐2‐yn‐1‐yl)selanes as substrates from moderate to excellent yields. A reasonable mechanism has been proposed according to literature data [193,194] and experimental evidence. First, on reaction with 2‐azidobenzaldehyde 202 , ortho ‐phenylenediamine 201 is transformed into imine A , while copper catalyst interacts with selenium‐containing alkyne to yield alkyne−copper complex B , which reacts with A to afford intermediate C that is further converted into D via a copper(I)‐catalyzed alkyne−azide cycloaddition [195,196] .…”

Pitfalls in the structural elucidation of small molecules. A critical analysis of a decade of structural misassignments of marine natural products

“…112 After this initial structural revision, a second one was provided during the synthesis of UGA 89 . 113,114 Again, the NMR spectra of the natural and the synthetic compounds were different, prompting a re-examination of the original NMR data and those for analogue 93 (Fig. 17).…”