Serendipitous Synthesis of (tert-Butyl-NNO-azoxy)acetonitrile: Reduction of an Oxime Moiety to a Methylene Unit

Serendipitous Synthesis of (tert-Butyl-NNO-azoxy)acetonitrile: Reduction of an Oxime Moiety to a Methylene Unit Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2016, Volume: 2016, Number: 22, Pages: 3845-3855 Pages count : 11 DOI: 10.1002/ejoc.201600584

Authors

Klenov Michael S. ¹ , Anikin Oleg V. ¹ , Guskov Alexey A. ¹ , Churakov Aleksandr M. ¹ , Strelenko Yurii A. ¹ , Ananyev Ivan V. ² , Bushmarinov Ivan S. ² , Dmitrienko Artem O. ² , Lyssenko Konstantin A. ¹ , Tartakovsky Vladimir A. ¹

Affiliations

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

(tert-Butyl-NNO-azoxy)acetonitrile (1) is a useful precursor for a number of nitrogen heterocycles. It was found that it could be obtained in good yield by treatment of the salts of (tert-butyl-NNO-azoxy)(hydroxyimino)acetonitrile with NH2OTs. It is the first case of one-step reduction of an oxime group to a methylene unit using an aminating agent. A plausible reaction mechanism is proposed. In addition, a new strategy for the tetrazole 1-oxide ring construction was developed. This involves a diazo-group transfer to the active-methylene unit of compound 1, followed by intramolecular coupling of the azoxy and diazo groups. The tetrazole structures were confirmed by X-ray diffraction analysis.

Klenov M.S. , Anikin O.V. , Guskov A.A. , Churakov A.M. , Strelenko Y.A. , Ananyev I.V. , Bushmarinov I.S. , Dmitrienko A.O. , Lyssenko K.A. , Tartakovsky V.A.
Serendipitous Synthesis of (tert-Butyl-NNO-azoxy)acetonitrile: Reduction of an Oxime Moiety to a Methylene Unit
European Journal of Organic Chemistry. 2016. V.2016. N22. P.3845-3855. DOI: 10.1002/ejoc.201600584 WOS Scopus OpenAlex

≡ Web of science:	WOS:000382768400025
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