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...

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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

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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

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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...

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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 Learn More

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

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

1,2,4-Oxadiazol...

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

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

~%

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

1,2,4-Oxadiazol...

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Benzenecarboximidamide,N-hydroxy-N'-methyl Structure

Benzenecarboxim...

~%

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

1,2,4-Oxadiazol...

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N-hydroxy-4-methyl-benzenecarboximidoyl chloride Structure

N-hydroxy-4-met...

~%

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

1,2,4-Oxadiazol...

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4-HYDROXYBUTYROPHENONE Structure

4-HYDROXYBUTYRO...

~%

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

1,2,4-Oxadiazol...

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N/A Structure

~%

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

1,2,4-Oxadiazol...

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(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...

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(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...

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(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...

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4-CHLORO-N-HYDROXYBENZIMIDOYL CHLORIDE Structure

4-CHLORO-N-HYDR...

~%

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

1,2,4-Oxadiazol...

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N-HYDROXY-4-METHOXYBENZENECARBOXIMIDOYL CHLORIDE Structure

N-HYDROXY-4-MET...

~%

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

1,2,4-Oxadiazol...

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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...

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(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...

Learn More

4-CHLORO-N-HYDROXYBENZIMIDOYL CHLORIDE Structure

4-CHLORO-N-HYDR...

~%

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

5-(4-chlorophen...

Learn More

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 Learn More

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 Learn More

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...

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N-hydroxy-4-methyl-benzenecarboximidoyl chloride Structure

N-hydroxy-4-met...

~%

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

5-(4-methylphen...

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N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

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

5-(4-methylphen...

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N/A Structure

~%

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

5-(4-methylphen...

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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 Learn More

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...

Learn More

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...

Learn More

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

Learn More

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

Learn More

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...

Learn More

4-HYDROXYBUTYROPHENONE Structure

4-HYDROXYBUTYRO...

~%

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

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

Learn More

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~%

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

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

Learn More

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...

Learn More

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...

Learn More

(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...

Learn More

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...

Learn More

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...

Learn More

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 Learn More

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 Learn More

methylamine Structure

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~0%

Benzenecarboximidamide,N-hydroxy-N'-methyl Structure

Benzenecarboxim...

Methylamine hydrochloride Structure

Methylamine hyd...

Learn More

methylamine Structure

N-Phenylbenzohydroxamic acid Structure

N-Phenylbenzohy...

~77%

Benzenecarboximidamide,N-hydroxy-N'-methyl Structure

Benzenecarboxim...

Methylamine hydrochloride Structure

Methylamine hyd...

Learn More

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 Learn More

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 Learn More

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 Learn More

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...

Learn More

(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...

Learn More

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

Learn More

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

Learn More

4-HYDROXYBUTYROPHENONE Structure

4-HYDROXYBUTYRO...

~%

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

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

Learn More

(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...

Learn More

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...

Learn More

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...

Learn More

morpholine Structure

Alpha-Chlorobenzaldoxime Structure

Alpha-Chloroben...

~0%

Morpholine hydrochloride Structure

Morpholine hydr...

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

4-(N-hydroxy-be...

Learn More

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

[Kivrak, Arif; Zora, Metin Tetrahedron, 2014 , vol. 70, # 4 p. 817 - 831]

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

[Kivrak, Arif; Zora, Metin Tetrahedron, 2014 , vol. 70, # 4 p. 817 - 831]

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...

[Wang, Yi-Feng; Zhang, Feng-Lian; Chiba, Shunsuke Organic Letters, 2013 , vol. 15, # 11 p. 2842 - 2845]