Short and efficient synthesis of 1-(2-oxido-1,2,5-oxadiazol-3-yl)alkyl nitrates by unconventional nitrooxylation of 3-alkyl-1,2,5-oxadiazole 2-oxides

Short and efficient synthesis of 1-(2-oxido-1,2,5-oxadiazol-3-yl)alkyl nitrates by unconventional nitrooxylation of 3-alkyl-1,2,5-oxadiazole 2-oxides Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2016, Volume: 57, Number: 36, Pages: 4027-4030 Pages count : 4 DOI: 10.1016/j.tetlet.2016.07.048

Authors

Ogurtsov Vladimir A. ¹ , Shastin Alexey V. ² , Zlotin Sergei G. ¹ , Rakitin Oleg A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2	Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation

A short and efficient synthesis of 1-(2-oxido-1,2,5-oxadiazol-3-yl)alkyl nitrates from 3-alkyl-1,2,5-oxadiazole 2-oxides, using a mixture of nitric and sulfuric acids in chloroform, has been developed. The scope of the unconventional reaction was established; its mechanism likely included a new Grob-type fragmentation.

Ogurtsov V.A. , Shastin A.V. , Zlotin S.G. , Rakitin O.A.
Short and efficient synthesis of 1-(2-oxido-1,2,5-oxadiazol-3-yl)alkyl nitrates by unconventional nitrooxylation of 3-alkyl-1,2,5-oxadiazole 2-oxides
Tetrahedron Letters. 2016. V.57. N36. P.4027-4030. DOI: 10.1016/j.tetlet.2016.07.048 WOS Scopus OpenAlex

Web of science:	WOS:000382338200011
Scopus:	2-s2.0-84981210907
OpenAlex:	W2474108997

DB	Citing
OpenAlex	13
Scopus	12
Web of science	12