Alkylation reactions of 5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones with alkyl halides

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2016-12, Vol.52 (12), p.1061-1069
• Main Authors: Parfenov, Victor E., Bakharev, Vladimir V., Gidaspov, Alexander A., Shiryaev, Andrey K., Slepukhin, Pavel A.
• Format: Article
• Language: English
• Subjects: Alkylation; Carbonyls; Chemical reactions; Chemistry; Chemistry and Materials Science; Functional groups; Halides; Nitrogen; Organic Chemistry; Pharmacy; Quantum chemistry; Ring opening; Substitutes; Tetrazoles
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-017-2007-y

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(3 H )-one with ethyl bromide are presented. The reactions of 5-aminosubstituted tetrazolo[1,5- a ][1,3,5]triazin-7(3 H )-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(3 H )-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-1 H -tetrazol-5-yl)- N '-alkyl- and N -(1-alkyl-1 H -tetrazol-5-yl)- N ', N '-dialkylguanidines.