Nucleophilic substitution in azasydnone-modified dinitroanisoles

Reactions of 3-(4-methoxy-3,5-dinitrophenyl)-1,2,3,4-oxatriazolium-5-olate with <em>N</em>-nucleophiles under mild conditions results in the displacement of the methoxy group leaving 1,2,3,4-oxatriazolium-5-olate (azasydnone) moiety intact. In the case of alkylhydrazines, further cyclization involving nitro group into benzo[<em>d</em>][1,2,3]triazole 3-oxides occurs.

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Publication Details

Journal
Mendeleev Communications
Published
2025-01-01
DOI
https://doi.org/10.71267/mencom.7614
Primary Topic
Chemical Reaction Mechanisms
Type
article
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article

Nucleophilic substitution in azasydnone-modified dinitroanisoles

Igor L. Dalinger, Tatyana K. Shkineva, Alexandr V. Kormanov
Mendeleev Communications
Chemical Reaction Mechanisms
article

Nucleophilic substitution in azasydnone-modified dinitroanisoles

Igor L. Dalinger, Tatyana K. Shkineva, Alexandr V. Kormanov
article en

Abstract

Reactions of 3-(4-methoxy-3,5-dinitrophenyl)-1,2,3,4-oxatriazolium-5-olate with <em>N</em>-nucleophiles under mild conditions results in the displacement of the methoxy group leaving 1,2,3,4-oxatriazolium-5-olate (azasydnone) moiety intact. In the case of alkylhydrazines, further cyclization involving nitro group into benzo[<em>d</em>][1,2,3]triazole 3-oxides occurs.

Mendeleev CommunicationsVol. 35(3)
N.D. Zelinsky Institute of Organic Chemistry (RU)
Openalex Percentile: Top 95%
Chemical Reaction Mechanisms
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