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Synthesis 2000; 2000(5): 681-690
DOI: 10.1055/s-2000-6399
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Intramolecular Cyclization of 1,2-bis(N-alkoxy-N-nitrosoamino)alkanes: A Unique Route to 4,5-Dihydro-1,2,3-triazole 2-Oxides

Vadim K. Khlestkin* , Dmitrii G. Mazhukin, Alexsei Ya. Tikhonov, Tatyana V. Rybalova, Irina Yu. Bagryanskaya, Yurii V. Gatilov
  • *N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Lavrent'eva prosp., 9, Novosibirsk 630090, Russia; Fax + 7(3832)34 47 52; E-mail: vadim@nioch.nsc.ru
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Publication Date:
31 December 2000 (online)

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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.

1,2-bisalkoxyamines - 1,2-bis(N-alkoxy-N-nitroso)amines - 1,2-bis(nitrosohydroxylamines) - 1,2,3-triazole 2-oxides - intramolecular cyclization - nitrogen - nitrosation - heterocycles

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