Synthesis and alkylation reaction of 1-arylmethyleneamino- and 1-arylsulfonyl-5-hydroxy-1H-1,2,3-triazoles / Rozin Y.A., Savel'eva E.A., Morzherin Y., Dehaen W., Toppet S., Meervelt L.V., Bakulev V.A. // Journal of the Chemical Society. Perkin Transactions 1. - 2002. - V. 2, l. 2. - P. 211-216.

ISSN:

14727781

Type:

Article

Abstract:

New derivatives of 1H-1,2,3-triazole 4,6,7 were prepared from malonic acid derivatives by a diazo group transfer reaction with p-tosyl azide. It was found that alkylation of sodium 1-aryl- and 1-arylmethyleneamino-1,2,3-triazol-5-olates 7,4 with methyl iodide, benzyl chloride or substituted phenacyl bromides results in 3-alkyltriazol-3-ium-5-olates 8,9 that are compounds of mesoionic structure. In contrast, alkylation of 1-arylsulfonyl-substituted triazoles 6 with methyl iodide leads to the 2-methyl-1,2-dihydro-1,2,3-triazol-5-ones 12. Hydrolysis of azomethines 9 affords 1-aminotriazoles 10, which in turn can be deaminated by nitrous acid or butyl nitrite to give 1-alkyl-4-hydroxytriazoles 11.

Author keywords:

Index keywords:

Alkylation; Amino acids; Hydrolysis; Molecular structure; Synthesis (chemical); Intermediate compounds; Aromatic hydrocarbons

DOI:

10.1039/b108202g

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0036007059&doi=10.1039%2fb108202g&partnerID=40&md5=5645a0977a3eeedb6ba6026bcc4c0887

Соавторы в МНС:

Другие поля

Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0036007059&doi=10.1039%2fb108202g&partnerID=40&md5=5645a0977a3eeedb6ba6026bcc4c0887
Affiliations	The Urals State Technical University, 620002 Ekaterinburg, Russian Federation; Department of Chemistry, Celestijnenlaan 200F, B-3001 Leuven, Belgium
References	Montgomery, J.A., (1980) Triazoles: 1, 2, 3, , John Wiley & Sons, Chichester; Rozin, Yu.A., Vorob'Eva, E.A., Morzherin, Yu.Yu., Yakimov, A.S., Dehaen, W., Bakulev, V.A., (1998) Mendeleev Commun., p. 240; Begtrup, M., Hansen, K., Pedersen, C., (1967) Acta Chem. Scand., 21, p. 1234; Begtrup, M., (1969) Acta Chem. Scand., 23, p. 2025; Begtrup, M., Pedersen, C., (1967) Acta Chem. Scand., 21, p. 633; Begtrup, M., (1974) Acta Chem. Scand., Ser. B, 28, p. 61; Begtrup, M., Pedersen, C., (1969) Acta Chem. Scand., 23, p. 1091; Bakulev, V.A., Morzherin, Yu.Yu., Lebedev, A.T., Dankova, E.F., Kolobov, M.Yu., Shafran, Yu.M., (1993) Bull. Soc. Chim. Belg., 102, p. 493; L'Abbe, G., Delbeke, P., Van Essche, G., Luyten, I., Vercauteren, K., Toppet, S., (1990) Bull. Soc. Chim. Belg., 99, p. 1007; Saalfrank, R.W., Weiss, B., Wirth, V., Peters, K., Von Schering, H.G., (1989) Z. Naturforsch., Teil B, 44, p. 587
Language of Original Document	English
Abbreviated Source Title	J Chem Soc Perkin Trans 1
Source	Scopus