An unusual reduction of azido group accompanied by ring closure to 1,2,3-triazole 3-oxide


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Аннотация

The reaction of 2-[(2-azidophenyl)hydrazono]-2-(tert-butyl-NNO-azoxy)-N′-hydr oxyethanimidamide with sodium acetate in DMF aff ords 2-(2-aminophenyl)-5-(tert-butyl-NNO-azoxy)-2H-1,2,3-triazol-4-amine 3-oxide rather than the anticipated 2-(2-azidophenyl)-5- (tert-butyl-NNO-azoxy)-2H-1,2,3-triazol-4-amine. The formation of this product can be explained by intramolecular reduction of azido to amino group and cyclization of an inter mediate vicinal (azo)nitrosoethylene into a triazole 3-oxide ring. The structure of aminotriazole 3-oxide 10 was confirmed by X-ray diff raction and NMR spectroscopy.

Авторлар туралы

A. Konnov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: octy@xrlab.ineos.ac.ru
Ресей, 47 Leninskii prosp., Moscow, 119991

M. Klenov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: octy@xrlab.ineos.ac.ru
Ресей, 47 Leninskii prosp., Moscow, 119991

A. Churakov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: churakov@ioc.ac.ru
Ресей, 47 Leninskii prosp., Moscow, 119991

Yu. Strelenko

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: octy@xrlab.ineos.ac.ru
Ресей, 47 Leninskii prosp., Moscow, 119991

I. Fedyanin

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: octy@xrlab.ineos.ac.ru
Ресей, 28 ul. Vavilova, Moscow, 119991

V. Tartakovsky

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: octy@xrlab.ineos.ac.ru
Ресей, 47 Leninskii prosp., Moscow, 119991

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