Selective Synthesis of 3‐Bulkyalkylsubstituted 5‐Aminoisoxazol

Rouchaud, Jean; Gustin, F.; Moulard, Claude

doi:10.1002/bscb.19931020807

Bulletin des Soc Chimique

1993

DOI: 10.1002/bscb.19931020807

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Selective Synthesis of 3‐Bulkyalkylsubstituted 5‐Aminoisoxazol

Jean Rouchaud

F. Gustin

Claude Moulard

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Cited by 4 publications

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“…Examples are known of applying β-cyanoximes in the preparation of 5-aminoisoxazoles [1,2], including the condensed ones [3], and also the derivatives of indole [4], azarine [5], 5-amino-1,3-oxazole, pyrrolidinone, and oxazolo [5,4-b]pyridine [6]. Usually the cyanoximes are obtained from ketonitriles [4,7,8] or enaminonitriles [1] and hydroxylamine, and also by reduction of β-nitrocyanides [9].…”

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Synthesis and properties of vicinal cyanoximes of adamantane series

2015

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1,4-Addition of cyanide ion to conjugated nitrosoalkenes of adamantane series, generated in situ from dimers of 2-alkylideneadamantanes nitroso chlorides or from α-chloro-oxime, results in vicinal cyanoximes. Proceeding from the latter approaches to some 2,2-disubstituted adamantanes were developed.The presence of two reactive groups in the structure of vicinal cyanoximes makes them promising synthons in heterocyclization processes. Examples are known of applying β-cyanoximes in the preparation of 5-aminoisoxazoles [1, 2], including the condensed ones [3], and also the derivatives of indole [4], azarine [5], 5-amino-1,3-oxazole, pyrrolidinone, and oxazolo[5,4-b]-pyridine [6]. Usually the cyanoximes are obtained from ketonitriles [4, 7, 8] or enaminonitriles [1] and hydroxylamine, and also by reduction of β-nitrocyanides [9]. At the same time there are only few known examples of their preparation from β-nitroso chlorides and inorganic cyanides [10-13].In extension of investigations on the chemical properties of nitroso chlorides of adamantane series [14-16] we studied the reaction of dimeric nitroso chlorides of 2-alkylideneadamantanes 1a and 1b or chloro-oxime 2 with excess of sodium cyanide in DMF that resulted in vicinal cyanoximes 3a-3с (Scheme 1) in high yield.The reaction mechanism evidently includes the generation of unstable nitrosoalkenes A [17,18], then the cyanide ion adds to them by Michael reaction. In the IR spectra of cyanoderivatives 3а-3с characteristic absorption bands are present at 2230-2245 cm -1 , corresponding to vibrations of the cyano group. In 13 С NMR spectra the atoms of carbon of cyano and oxime groups appear in the region 121.0-122.2 and 149.9-158.5 ppm respectively. The hydrogen atom of the hydroxy group of oxime fragment is detected in 1 Н NMR spectra at 8.05-8.51 ppm. (in CDCl 3 solution).Treating α-cyanoxime 3а with thionyl chloride in the presence of triethylamine afforded adamantane-2,2-dicarbonyl 4. Amide of 2-cyano-2-adamantanecarboxylic acid 5 was obtained by heating α-cyanoxime 3а in DMF above 130°С (Scheme 2). Since no acid catalyst is present the generation of amide 5 cannot result from Beckmann rearrangement that also should have provided a substituted formamide of oxime 3a of Е-configuration.We assume that first the isomerization of oxime in Z-form occurs. Such process may proceed in DMF at high temperature because the barrier to E,Z-isomerization in oximes is relatively low [19]. Further as

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Synthesis and properties of vicinal cyanoximes of adamantane series

2015

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ChemInform Abstract: Selective Synthesis of 3‐Bulkyalkylsubstituted 5‐Aminoisoxazole.

1994

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Selective Synthesis of 3-Bulkyalkylsubstituted 5-Aminoisoxazole. -While cyclization of the ketonitrile (I) under weakly acidic conditions leads to a mixture of compounds (II), (III) and (IV) the title compound (III) can be prepared almost exclusively by reaction of the 3-ketonitrile (I) with a 1:1 ratio of hydroxylamine hydrochloride and sodium hydroxide followed by acidic hydrolysis. -(ROUCHAUD, J.; GUSTIN, F.; MOULARD, C.; Bull. Soc. Chim. Belg. 102 (1993) 8, 545-555; Lab. Phytopharm., Univ. Cathol. Louvain, Louvain-la-Neuve, Belg.; EN)

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Synthesis of diverse isoxazolylamino-2-(aryl)acetamides using one-pot Multicomponent Reactions: X-ray, Hirshfeld analysis and DFT modeling

Loubidi

Jouha

Hdoufane

et al. 2020

Journal of Molecular Structure

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Selective Synthesis of 3‐Bulkyalkylsubstituted 5‐Aminoisoxazol

Cited by 4 publications

References 10 publications

Synthesis and properties of vicinal cyanoximes of adamantane series

Synthesis and properties of vicinal cyanoximes of adamantane series

ChemInform Abstract: Selective Synthesis of 3‐Bulkyalkylsubstituted 5‐Aminoisoxazole.

Synthesis of diverse isoxazolylamino-2-(aryl)acetamides using one-pot Multicomponent Reactions: X-ray, Hirshfeld analysis and DFT modeling

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