Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade

Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2020, Volume: 85, Number: 23, Pages: 15466-15475 Pages count : 10 DOI: 10.1021/acs.joc.0c02243

Authors

Bystrov Dmitry M. ¹ , Ananyev Ivan V. ^2,3 , Fershtat Leonid L. ¹ , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russia
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, Moscow 119991, Russia
3	Plekhanov Russian University of Economics, Stremyanny Per. 36, Moscow 117997, Russia

A straightforward synthesis of a series of previously unknown N-(1,2,5-oxadiazolyl)hydrazones through the diazotization/reduction/condensation cascade of amino-1,2,5-oxadiazoles was accomplished. The described protocol was suitable for a wide array of target hydrazones, which were prepared in good to high yields under smooth reaction conditions with very good functional group tolerance. Importantly, the presented approach unveils a direct route to in situ generation of previously inaccessible (1,2,5-oxadiazolyl)hydrazines. In addition, a first example of the ionic structure incorporating a protonated hydrazone motif linked to the 1,2,5-oxadiazole 2-oxide subunit was synthesized, indicating the stability of prepared compounds toward acid-promoted hydrolysis. Overall, this method provides a direct access to the isosteric analogues of drug candidates for treatment of various neglected diseases, thus enabling their potential application in medicinal chemistry and drug design.

Bystrov D.M. , Ananyev I.V. , Fershtat L.L. , Makhova N.N.
Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade
Journal of Organic Chemistry. 2020. V.85. N23. P.15466-15475. DOI: 10.1021/acs.joc.0c02243 WOS Scopus OpenAlex

Web of science:	WOS:000598137400057
Scopus:	2-s2.0-85096602111
OpenAlex:	W3098725103

DB	Citing
OpenAlex	9
Scopus	7
Web of science	6