Alkylation reactions of 5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones with alkyl halides
| Autor: | Victor E. Parfenov, A. K. Shiryaev, Alexander A. Gidaspov, Pavel A. Slepukhin, Vladimir V. Bakharev |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry Organic Chemistry Halide Alkylation 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Bromide Functional group Tetrazole Alkyl Triazine |
| Zdroj: | Chemistry of Heterocyclic Compounds. 52:1061-1069 |
| ISSN: | 1573-8353 0009-3122 |
| Popis: | The alkylation reactions of fused tetrazolo[1,5-a][1,3,5]triazine system were studied. The results of quantum-chemical calculations for the reaction of 5-(dimethylamino)tetrazolo[1,5-a][1,3,5]triazin-7(3H)-one with ethyl bromide are presented. The reactions of 5-aminosubstituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones with ethyl-, butyl-, and allyl halides led to the formation of products due to alkylation at the N-3 nitrogen atom of the ring system, 3-alkyl-5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones, as well as products due to alkylation at the exocyclic oxygen atom with tetrazole ring opening, 2-amino-substituted 6-alkoxy-4-azido-1,3,5-triazines. Besides that, the product that was alkylated at the ring N-3 nitrogen atom underwent hydrolytic cleavage of the 1,3,5-triazine ring with elimination of the carbonyl functional group and formation of N-(1-alkyl-1H-tetrazol-5-yl)-N'-alkyl- and N-(1-alkyl-1H-tetrazol-5-yl)-N',N'-dialkylguanidines. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|