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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2019, Volume: 68, Number: 1, Pages: 191-193 Pages count : 3 DOI: 10.1007/s11172-019-2437-z

Authors

Konnov A.A. ¹ , Klenov M.S. ¹ , Churakov A.M. ¹ , Strelenko Yu.A. ¹ , Fedyanin Ivan V. ² , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninskii prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation

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.

Konnov A.A. , Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Fedyanin I.V. , Tartakovsky V.A.
An unusual reduction of azido group accompanied by ring closure to 1,2,3-triazole 3-oxide
Russian Chemical Bulletin. 2019. V.68. N1. P.191-193. DOI: 10.1007/s11172-019-2437-z WOS Scopus OpenAlex

≡ Web of science:	WOS:000464854400030
≡ Scopus:	2-s2.0-85064342034
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