Intramolecular cyclization of 1,2-bis(N-alkoxy-N-nitrosoamino)alkanes: A unique route to 4,5-dihydro-1,2,3-triazole 2-oxides

Intramolecular cyclization of 1,2-bis(N-alkoxy-N-nitrosoamino)alkanes: A unique route to 4,5-dihydro-1,2,3-triazole 2-oxides Full article

Journal

Synthesis
ISSN: 0039-7881

Output data

Year: 2000, Number: 5, Pages: 681-690 Pages count : 10 DOI: 10.1055/s-2000-6399

Tags

1,2,3-triazole 2-oxides; 1,2- bis(nitrosohydroxylamines); 1,2-bis(N-alkoxy-N-nitroso)amines; 1,2-bisalkoxyamines; Hererocycles; Intramolecular cyclization; Nitrogen; Nitrosation

Authors

Khlestkin V.K. , Mazhukin D.G. , Tikhonov A.Ya. , Rybalova T.V. , Bagryanskaya I.Yu. , Gatilov Y.V.

Affiliations

1	(Scopus) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Lavrent'eva prosp., 9, Novosibirsk 630090, Russian Federation

1,2-Bis(N-alkoxy-N-nitroso)amines 7 obtained by nitrosation of the corresponding 1,2-bisalkoxyamines 4 were smoothly converted into 1-alkoxy- 4,5-dihydro-1,2,3-triazole 2-oxides 8 under reflux in methanol in high yields. 4H-1,2,3-Triazole 2-oxides 9, a novel type of triazole oxides, and 2- hydroxy-2H-1,2,3-triazoles 10 were obtained by the reaction of 1-alkoxy-4,5- dihydro-1,2,3-triazole 2-oxides 8 with sodium methoxide.

Khlestkin V.K. , Mazhukin D.G. , Tikhonov A.Y. , Rybalova T.V. , Bagryanskaya I.Y. , Gatilov Y.V.
Intramolecular cyclization of 1,2-bis(N-alkoxy-N-nitrosoamino)alkanes: A unique route to 4,5-dihydro-1,2,3-triazole 2-oxides
Synthesis. 2000. N5. P.681-690. DOI: 10.1055/s-2000-6399 WOS Scopus РИНЦ

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