e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazole-4-oxides.

P Quadrelli, AG Invernizzi, M Falzoni, P Caramella

Index: Quadrelli, Paolo; Invernizzi, Anna Gamba; Falzoni, Mario; Caramella, Pierluigi Tetrahedron, 1997 , vol. 53, # 5 p. 1787 - 1796

Full Text: HTML

Citation Number: 27

Abstract

The cycloaddition of nitrile oxides to amidoximes is a general method for the sinthesis of 3, 5- disubstituted 1, 2, 4-oxadiazole-4-oxides with the same or different substituents. The yields are only moderate since an equivalent amount of the nitrile oxide is consumed by reaction with the amine released in the fragmentation of the primary cycloadducts and reforms the amidoxime. With excess nitrile oxides the 1, 2, 4-oxadiazole-4-oxides undergo a ...

Alpha-Chlorobenzaldoxime Structure

Alpha-Chloroben...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

~61%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

N/A Structure

9,10-Dimethylanthracene Structure

9,10-Dimethylan...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~62%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

N/A Structure

9,10-Dimethylanthracene Structure

9,10-Dimethylan...

potassium salt of 2,2-dicyano-N-methylacetamide Structure

potassium salt ...

~59%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

N-(4-chlorobenzoyl)-9,10-dihydro-9,10-dimethyl-9,10-epoxyiminoanthracene Structure

N-(4-chlorobenz...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

4-(N-hydroxy-benzimidoyl)-morpholine Structure

4-(N-hydroxy-be...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

(E)-N,N-Dimethylbenzamid-oxim Structure

(E)-N,N-Dimethy...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

Benzenecarboximidamide,N-hydroxy-N'-methyl- Structure

Benzenecarboxim...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

N-hydroxy-4-methyl-benzenecarboximidoyl chloride Structure

N-hydroxy-4-met...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-HYDROXYBUTYROPHENONE Structure

4-HYDROXYBUTYRO...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

N/A Structure

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

(E)-4-chloro-N,N-diethyl-N'-hydroxybenzimidamide Structure

(E)-4-chloro-N,...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

(E)-N,N-diethyl-N'-hydroxy-4-methoxybenzimidamide Structure

(E)-N,N-diethyl...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

(E)-N,N-diethyl-N'-hydroxy-4-nitrobenzimidamide Structure

(E)-N,N-diethyl...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-CHLORO-N-HYDROXYBENZIMIDOYL CHLORIDE Structure

4-CHLORO-N-HYDR...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

N-HYDROXY-4-METHOXYBENZENECARBOXIMIDOYL CHLORIDE Structure

N-HYDROXY-4-MET...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

5-(4-chlorophenyl)-3-methyl-1,2,4-oxadiazole 4-oxide Structure

5-(4-chlorophen...

~%

5-(4-chlorophenyl)-3-methyl-1,2,4-oxadiazole Structure

5-(4-chlorophen...

(E)-4-chloro-N,N-diethyl-N'-hydroxybenzimidamide Structure

(E)-4-chloro-N,...

~%

5-(4-chlorophenyl)-3-methyl-1,2,4-oxadiazole Structure

5-(4-chlorophen...

4-CHLORO-N-HYDROXYBENZIMIDOYL CHLORIDE Structure

4-CHLORO-N-HYDR...

~%

5-(4-chlorophenyl)-3-methyl-1,2,4-oxadiazole Structure

5-(4-chlorophen...

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~0%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

benzonitrile oxide Structure

benzonitrile oxide

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

3-phenyl-5-p-tolyl-1,2,4-oxadiazole-4-oxide Structure

3-phenyl-5-p-to...

~%

5-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazole Structure

5-(4-methylphen...

N-hydroxy-4-methyl-benzenecarboximidoyl chloride Structure

N-hydroxy-4-met...

~%

5-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazole Structure

5-(4-methylphen...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

5-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazole Structure

5-(4-methylphen...

N/A Structure

~%

5-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazole Structure

5-(4-methylphen...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

4-(N-hydroxy-benzimidoyl)-morpholine Structure

4-(N-hydroxy-be...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~0%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

3-phenyl-5-p-tolyl-1,2,4-oxadiazole-4-oxide Structure

3-phenyl-5-p-to...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

N/A Structure

~0%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

3-phenyl-5-p-tolyl-1,2,4-oxadiazole-4-oxide Structure

3-phenyl-5-p-to...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

(E)-4-chloro-N,N-diethyl-N'-hydroxybenzimidamide Structure

(E)-4-chloro-N,...

~0%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

N/A Structure

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

(E)-N,N-diethyl-N'-hydroxy-4-methoxybenzimidamide Structure

(E)-N,N-diethyl...

~0%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

N/A Structure

N-hydroxy-4-methyl-benzenecarboximidoyl chloride Structure

N-hydroxy-4-met...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

4-HYDROXYBUTYROPHENONE Structure

4-HYDROXYBUTYRO...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

4-CHLORO-N-HYDROXYBENZIMIDOYL CHLORIDE Structure

4-CHLORO-N-HYDR...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

N-HYDROXY-4-METHOXYBENZENECARBOXIMIDOYL CHLORIDE Structure

N-HYDROXY-4-MET...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

(E)-N,N-Dimethylbenzamid-oxim Structure

(E)-N,N-Dimethy...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

N-Hydroxybenzenecarboximidamide Structure

N-Hydroxybenzen...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Benzenecarboximidamide,N-hydroxy-N'-methyl- Structure

Benzenecarboxim...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~43%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

benzonitrile oxide Structure

benzonitrile oxide

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

methylamine Structure

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~0%

Benzenecarboximidamide,N-hydroxy-N'-methyl- Structure

Benzenecarboxim...

Methylamine hydrochloride Structure

Methylamine hyd...

methylamine Structure

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~77%

Benzenecarboximidamide,N-hydroxy-N'-methyl- Structure

Benzenecarboxim...

Methylamine hydrochloride Structure

Methylamine hyd...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

4-(N-hydroxy-benzimidoyl)-morpholine Structure

4-(N-hydroxy-be...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~0%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

benzonitrile oxide Structure

benzonitrile oxide

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

~%

1,2,4-Oxadiazole,3,5-diphenyl- Structure

1,2,4-Oxadiazol...

4-oxido-3,5-diphenyl-1,2,4-oxadiazol-4-ium Structure

4-oxido-3,5-dip...

Detail

N-hydroxy-4-methyl-benzenecarboximidoyl chloride Structure

N-hydroxy-4-met...

~%

3,5-bis(4-methylphenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-methy...

(E)-N,N-diethyl-N'-hydroxy-4-nitrobenzimidamide Structure

(E)-N,N-diethyl...

N/A Structure

~27%

3,5-bis(4-nitrophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-nitro...

N/A Structure

~0%

3,5-bis(4-nitrophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-nitro...

N/A Structure

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

N/A Structure

~0%

3,5-bis(4-nitrophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-nitro...

N/A Structure

4-HYDROXYBUTYROPHENONE Structure

4-HYDROXYBUTYRO...

~%

3,5-bis(4-nitrophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-nitro...

(E)-4-chloro-N,N-diethyl-N'-hydroxybenzimidamide Structure

(E)-4-chloro-N,...

potassium salt of 2,2-dicyano-N-methylacetamide Structure

potassium salt ...

~33%

3,5-bis(4-chlorophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-chlor...

potassium salt of 2,2-dicyano-N-methylacetamide Structure

potassium salt ...

~0%

3,5-bis(4-chlorophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-chlor...

3-(4-chlorophenyl)-5-phenyl-1,2,4-oxadiazole 4-oxide Structure

3-(4-chlorophen...

N,N-diethylamino benzamidoxime Structure

N,N-diethylamin...

potassium salt of 2,2-dicyano-N-methylacetamide Structure

potassium salt ...

~0%

3,5-bis(4-chlorophenyl)-4-oxido-1,2,4-oxadiazol-4-ium Structure

3,5-bis(4-chlor...

3-(4-chlorophenyl)-5-phenyl-1,2,4-oxadiazole 4-oxide Structure

3-(4-chlorophen...

morpholine Structure

Alpha-Chlorobenzaldoxime Structure

Alpha-Chloroben...

~0%

Morpholine hydrochloride Structure

Morpholine hydr...

4-(N-hydroxy-benzimidoyl)-morpholine Structure

4-(N-hydroxy-be...

5-phenyl-3-p-tolyl-1,2,4-oxadiasole-4-oxide Structure

5-phenyl-3-p-to...

~%

3-(4-methylphenyl)-5-phenyl-1,2,4-oxadiazole Structure

3-(4-methylphen...

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A novel synthesis of 1, 2, 4-oxadiazoles and isoxazoles

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Hypervalent iodine catalyzed generation of nitrile oxides fr...

[Yoshimura, Akira; Middleton, Kyle R.; Todora, Anthony D.; Kastern, Brent J.; Koski, Steven R.; Maskaev, Andrey V.; Zhdankin, Viktor V. Organic Letters, 2013 , vol. 15, # 15 p. 4010 - 4013]

Orthogonal aerobic conversion of N-benzyl amidoximes to 1, 2...

[Zhang, Feng-Lian; Wang, Yi-Feng; Chiba, Shunsuke Organic and Biomolecular Chemistry, 2013 , vol. 11, # 36 p. 6003 - 6007]

Sulfate Radical Anion (SO4•–) Mediated C (sp3)–H Nitrogenati...

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