Synthesis of new azepanedione oximes

Abstract

Synthesis and physico-chemical properties of some l-benzyl-azepane-2,3-dione 3-(O-substituted oximes) with attribution of their Ζ and Ε configurations and 4-(phenylhydrazono)azepane-2,3-dione 3-(0-substituted oximes) resulting of condensation with various O-aryl-hydroxylamines are described. These azepanedione-oxime compounds are prepared from the corresponding azepan-2-ones and 1-benzylazepan-2-ones. IntroductionThrough studies of amide or lactame derivatives highlighted the interesting pharmacological properties, in particular actions on central nervous system via stimulation of various ion channels [1], The synthesis of 3-[0-(benzyl)oximinoether] hexahydroazepin-2,3-diones previously reported [2] showed that they are capable to relax both rat trachea and human bronchus. The oximinoether or oxime derivatives exhibited marked antinociceptive and anticonvulsant activities [3], This work describes synthesis and physicochemical properties of l-benzylazepane-2,3-dione 3-(0-substituted oximes) with attribution of their Ζ and Ε configurations and 4-(phenylhydrazono)azepane-2,3-dione 3-(0-substituted oximes) resulting of condensation with various O-arylhydroxylamines from the corresponding azepan-2-ones and 1 -benzylazepan-2-ones.

Oximes of Seven-Membered Heterocyclic Compounds Containing One Heteroatom

“…Azepane oximes 2 have been obtained in the two-step reaction from the acid 1 in the presence of polyphosphoric acid (PPA) and hydroxylamine hydrochloride [6]. 3-Oxime of 4-(phenylhydrazino)azepan-2,3-dione (6) has been prepared in two steps by amination of morpholine derivative 5 in the presence of phenylhydrazine and hydroxylamine hydrochloride [9]. Interaction of enamine 7 with hydroxylamine hydrochloride affords oxime derivative 8 in 50% yield [10].…”

“…Beside this O-ethers of azepane oximes are obtained from the corresponding carbonyl compounds and O-alkyl derivatives of hydroxylamine in the presence of pyridine in methanol [43], pyridine in ethanol [9] or sodium acetate in acetic acid [44]. Reaction of oxime of azepan-2-one with dimethyl acetylenedicarboxylate (DMAD) in acetonitrile gives a mixture of Eand Z-isomers of oxime ethers 28 and 29 in the ratio 8:1 [45].…”