Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles

Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2022, Volume: 103, Article number : 132563, Pages count : DOI: 10.1016/j.tet.2021.132563

Authors

Titenkova Kseniia Yu ^1,2 , Shaferov Alexander V. ² , Larin Alexander A. ² , Epishina Margarita A. ² , Kulikov Alexander S. ² , Ananyev Ivan V. ^3,4 , Fershtat Leonid L. ²

Affiliations

1	Department of Chemistry, Moscow State University, 119991, Leninskie Gory 1-3, Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prosp., 47, Moscow, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str., 28, Moscow, Russia
4	Plekhanov Russian University of Economics, 117997, Stremyanny per. 36, Moscow, Russia

A general method for the synthesis of a series of previously unknown N-(heteroaryl)- and N-(aryl)aminotetrazoles through the tandem electrocyclization/hydrolysis of azidohydrazones was accomplished. The described protocol was suitable for a wide array of the target N-substituted aminotetrazoles which were prepared in good to high yields under smooth reaction conditions. Importantly, the presented approach is considered as a direct route to 1,2,5-oxadiazole-substituted aminotetrazole derivatives in good and high yields and may be realized on a gram scale. Therefore, facile synthesis of N-(heteroaryl)- and N-(aryl)aminotetrazoles unveils novel opportunities to study application prospectives of these compounds as functional materials or drug candidates.

Titenkova K.Y. , Shaferov A.V. , Larin A.A. , Epishina M.A. , Kulikov A.S. , Ananyev I.V. , Fershtat L.L.
Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles
Tetrahedron. 2022. V.103. 132563 . DOI: 10.1016/j.tet.2021.132563 WOS Scopus OpenAlex

Web of science:	WOS:000727184000016
Scopus:	2-s2.0-85119447084
OpenAlex:	W3212191055

DB	Citing
OpenAlex	4
Scopus	4
Web of science	3