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ALKYLATION REACTIONS OF 5-AMINOSUBSTITUTED TETRAZOLO[1,5-a][1,3,5]TRIAZIN-7(3Н)-ONES WITH ALKYL HALIDES

Виктор Е. Парфенов, Владимир В. Бахарев, Александр А. Гидаспов, Андрей К. Ширяев, Павел А. Слепухин
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Abstract


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(3Н)-one with ethyl bromide are presented. The reactions of 5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3Н)-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.

Authors: Victor E. Parfenov, Vladimir V. Bakharev*, Alexander A. Gidaspov, Andrei K. Shiryaev, Pavel A.  Slepukhin


Keywords


3-alkyl-5-aminotetrazolo[1,5-a][1,3,5]triazin-7(3Н)-ones; N-(1-alkyl-1H-tetrazol-5-yl)-N'-alkylguanidine; N-(1-alkyl-1H-tetrazol-5-yl)-N',N'-dialkylguanidines; 2-amino-6-alkoxy-4-azido-1,3,5-triazines; tetrazolo[1,5-a][1,3,5]triazines; alkylation; cleavage of 1,3,5-triazine ring

Full Text: PDF (Russian) Supplementary File(s): Supporting information (3MB)


 

 

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