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

Chemische Berichte

Ringöffnungen der Azole, II. Die Bildung von 1.3. 4??Oxdiazolen bei der Acylierung 5??substituierter Tetrazole

R Huisgen, J Sauer, HJ Sturm…

Index: Huisgen,R. et al. Chemische Berichte, 1960 , vol. 93, p. 2106 - 2124

Full Text: HTML

Citation Number: 201

Abstract

Abstract Die Einwirkung von Carbonsäure-chloriden oder-anhydriden auf 5-substituierte Tetrazole führt zu Derivaten des 1.3. 4-Oxdiazols in vorzüglicher Ausbeute. Die als Zwischenstufen nachweisbaren N-Acyl-tetrazole erleiden im Einklang mit theoretischen Überlegungen schon bei 60–130, je nach der Natur der Substituenten, eine Ringsprengung. Die Abgabe von Stickstoff führt zu N-Acyl-nitriliminen als hypothet. Zwischenstufen, die ...

Succinic anhydride Structure

Succinic anhydride

5-Phenyl-1H-tetrazole Structure

5-Phenyl-1H-tet...

~%

3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoic acid Structure

3-(5-phenyl-1,3...

Acetyl chloride Structure

Acetyl chloride

5-(4-NITROPHENYL)-1H-TETRAZOLE Structure

5-(4-NITROPHENY...

~%

2-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-Methyl-5-(4-n...

5-(4-Methylphenyl)-1H-tetrazole Structure

5-(4-Methylphen...

2-Nitrobenzoyl chloride Structure

2-Nitrobenzoyl ...

~%

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

2-(4-methylphen...

N,N-dimethyl-4-(2H-tetrazol-5-yl)aniline Structure

N,N-dimethyl-4-...

Benzoyl chloride Structure

Benzoyl chloride

~%

N,N-dimethyl-4-(5-phenyl-1,3,4-oxadiazol-2-yl)aniline Structure

N,N-dimethyl-4-...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

2H-Tetrazole,5-(4-methoxyphenyl)- Structure

2H-Tetrazole,5-...

~%

2-(4-methoxyphenyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-(4-methoxyphe...

p-toluoyl chloride Structure

p-toluoyl chloride

5-(4-Methylphenyl)-1H-tetrazole Structure

5-(4-Methylphen...

~%

1,3,4-Oxadiazole,2,5-bis(4-methylphenyl)- Structure

1,3,4-Oxadiazol...

Benzoyl chloride Structure

Benzoyl chloride

2H-Tetrazole,5-(4-methoxyphenyl)- Structure

2H-Tetrazole,5-...

~%

1,3,4-Oxadiazole,2-(4-methoxyphenyl)-5-phenyl- Structure

1,3,4-Oxadiazol...

Acetyl chloride Structure

Acetyl chloride

5-(4-Methylphenyl)-1H-tetrazole Structure

5-(4-Methylphen...

~%

1,3,4-Oxadiazole,2-methyl-5-(4-methylphenyl)- Structure

1,3,4-Oxadiazol...

Benzoyl chloride Structure

Benzoyl chloride

5-Methyl-1H-tetrazole Structure

5-Methyl-1H-tet...

~%

1,3,4-Oxadiazole, 2-methyl-5-phenyl- Structure

1,3,4-Oxadiazol...

Acetyl chloride Structure

Acetyl chloride

5-Phenyl-1H-tetrazole Structure

5-Phenyl-1H-tet...

~%

1,3,4-Oxadiazole, 2-methyl-5-phenyl- Structure

1,3,4-Oxadiazol...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

5-(4-Methylphenyl)-1H-tetrazole Structure

5-(4-Methylphen...

~%

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

2-(4-methylphen...

5-Phenyl-1H-tetrazole Structure

5-Phenyl-1H-tet...

2-Nitrobenzoyl chloride Structure

2-Nitrobenzoyl ...

~%

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

2-(2-nitropheny...

Benzoyl chloride Structure

Benzoyl chloride

5-(diphenylmethyl)-1H-tetrazole Structure

5-(diphenylmeth...

~%

2-benzhydryl-5-phenyl-1,3,4-oxadiazole Structure

2-benzhydryl-5-...

N,N-dimethyl-4-(2H-tetrazol-5-yl)aniline Structure

N,N-dimethyl-4-...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

N,N-dimethyl-4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]aniline Structure

N,N-dimethyl-4-...

Methyl 4-(2H-1,2,3,4-tetrazol-5-yl)benzoate Structure

Methyl 4-(2H-1,...

~%

4-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acid Structure

4-(5-Phenyl-1,3...

Benzoyl chloride Structure

Benzoyl chloride

~%

4-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acid Structure

4-(5-Phenyl-1,3...

Benzoyl chloride Structure

Benzoyl chloride

2H-Tetrazole,5-(1-methylethyl)- Structure

2H-Tetrazole,5-...

~%

2-Isopropyl-5-phenyl-1,3,4-oxadiazole Structure

2-Isopropyl-5-p...