Synthesis of oxaziridines by oxidation of imines with the trichloroacetonitrile–hydrogen peroxide system

Réaction des N-oxydes de 2-hydroxybenzylidènealkylamines avec l'isocyanate de chlorosulfonyle : synthèse de nouveaux composés hétérocycliques

“…L'oxydation des imines 3 par l'intermédiaire du système benzonitrileeeau oxygénée (50% en masse) conduit aux N-oxydes d'imines correspondantes 4 (Schéma 1). Ce système oxydant a été utilisé pour convertir les imines en oxaziridines [13,14], mais il s'est avéré que l'oxydation des N-arylidènealkylamines ayant un groupement hydroxyle en ortho du cycle benzénique par le système PhCN / H 2 O 2 aboutit à la formation des nitrones correspondant. Au cours de cette oxydation, nous n'avons pas observé de formation d'oxaziridines.…”

Three‐Membered Heterocycles. Structure and Reactivity

“…The sulfinylimine 788 was converted into sulfonyloxaziridine 789 in short order and in excellent yield using mCPBA in first acidic and then basic medium [771]. A trichloroacetonitrile-hydrogen peroxide system was found to convert imines such as 790 into oxaziridines in very high yield and exclusive (E)-stereochemistry under essentially neutral conditions [772]. Several other near-neutral systems are also available.…”

Synthesis and reactivity of new dihydroisoquinoline-derived oxaziridines

“…13 Oxaziridines can also be prepared by oxidation of imines with several oxidizing agents, such as cobalt-mediated molecular oxygen, 14 urea-hydrogen peroxide, 15 oxone, 16 hydrogen peroxide, 17 or a nitrilehydrogen peroxide system. 18 The oxidation of an imine with a peracid, usually meta-chloroperbenzoic acid (m-CPBA), is the most frequently employed method for oxaziridine preparation. 19 Since the first discovery of this function, 1 oxaziridines are well known as both aminating and oxygenating reagents in their reactions with a wide variety of nucleophiles and their structural electronic features.…”