Opening of the 1,3,5-triazine ring in 3-methyl-5-(trinitromethyl)tetrazolo[1,5-a][1,3,5]triazin-7-one by the action of alcohols

It was shown for the first time that in the reaction of 3-methyl-5-(trinitromethyl)tetrazolo[1,5- a ][1,3,5]triazin-7-one with alcohols in the presence of bases, along with the expected substitution of the trinitromethyl group, opening of the 1,3,5-triazine ring with the addition of an alcohol at th...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022, Vol.58 (2-3), p.153-158
Main Authors: Bakharev, Vladimir V., Gidaspov, Alexander А., Zalomlenkov, Vladimir А., Parfenov, Victor E., Golovina, Olga V., Slepukhin, Pavel А.
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Chemistry
Chemistry and Materials Science
Esters
Organic Chemistry
Pharmacy
Short Communication
Substitution reactions
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Summary:It was shown for the first time that in the reaction of 3-methyl-5-(trinitromethyl)tetrazolo[1,5- a ][1,3,5]triazin-7-one with alcohols in the presence of bases, along with the expected substitution of the trinitromethyl group, opening of the 1,3,5-triazine ring with the addition of an alcohol at the site of the C–N bond cleavage takes place. It was found that in the absence of bases only opening of the 1,3,5-triazine ring occurs with the formation of alkyl esters of {1-[(1-methyl-1 H -tetrazol-5-yl)imino]-2,2,2-trinitroethyl}carbamic acid, and the trinitromethyl group retains high reactivity and can be substituted by the action of alcohols in the presence of a base.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-022-03068-9