REACTIONS OF 3-NITRO-1,2,4-TRIAZOLES WITH ALKYLATING AGENTS. 6. ALKYLATION OF A NEUTRAL HETEROCYCLE BY ALCOHOLS IN ACID MEDIA

Authors

  • А. Г. Суханова Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biisk 659322
  • Г. В. Сакович Altai Federal State Unitary Enterprise, Federal Research & Production Center, Biisk 659322
  • Г. Т. Суханов Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biisk 659322

DOI:

https://doi.org/10.1007/7281

Keywords:

3-nitro-1, 2, 4-triazoles, alkylation, regioselectivity

Abstract

Reaction of 3-nitro-1,2,4-triazole and 5-methyl-3-nitro-1,2,4-triazole with secondary and tertiary alcohols in conc. H2SO4 takes place at the N(2) atom. Alkylation by 2-propanol occurs regioselectively to form the 1-isopropyl-3-nitro-  and 1-isopropyl-3-methyl-5-nitro-1,2,4-triazoles. As a consequence of isomerization the alkylation using cyclohexyl or tert-butyl alcohols gives respectively a mixture of regioisomers substituted at atom N(1) (1-cyclohexyl-3-nitro- and 1-cyclohexyl-5-methyl-3-nitro-1,2,4-triazoles) and at atom N(2) (5-nitro-1-cyclohexyl-  and 1-cyclohexyl-3-methyl-5-nitro-1,2,4-triazoles) and, in the second case, to 1-tert-butyl-3-nitro-1,2,4-triazole.

How to Cite
Sukhanova, A. G.; Sakovich, G. V.; Sukhanov, G. T.  Chem. Heterocycl. Compd. 2008, 44, 1368. [Khim. Geterotsikl. Soedin. 2008, 1680.]

For this article in the English edition see DOI 10.1007/s10593-009-0194-x

 

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Published

2023-01-04

Issue

No. 11 (2008)

Section

Original Papers