ChemInform Abstract: A NOVEL PREPARATION OF THE 1,3‐BENZOXAZEPINE RING SYSTEM

Abstract

Beim Erhitzen der Nitromethylbenzoxazinone (I) mit Salzsäure in siedendem Dioxan erfolgt eine Umlagerung zu Benzoxazinon‐oximen (ll).

Oximes of Seven-Membered Heterocyclic Compounds Containing Two Heteroatoms

“…Synthesis of 1,3-and 1,4-oxazepane oximes have been described in some articles [13][14][15][16][17]. Thus, interaction of oxepane ketone 15 with hydroxylamine hydrochloride in the presence of NaOAc/ EtOH leads to oxepane oxime 16 [13].…”

“…Reactions of hydroxylamine as an ambident nucleophile with 2,6-dimethyl-2,5-heptadien-4-one (19) was studied in details in the article [16] The treatment of oxazinones 24 with HCl gives colourless crystalline oximes 25 in 32 or 35% yield. The conversion of compound 24 to oxime 25 involves the loss of OH-group and the incorporation of chlorine atom [17]. …”

“…The 1 H NMR spectra of oximes of diazepane [5,8,12], oxazepane [17] and thiazepane [18] have been investigated in details.…”

“…Refluxing oxazepane oximes 25 in acetic anhydride affords corresponding O-acetyloximes 31 in 78-80 % yields [17]. …”