Chemical Reactions in Electrical Discharges by Gould R.F. (ed.)

By Gould R.F. (ed.)

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Bakulev VA, Lebedev AT, Dankova EF et al (1989) Two directions of cyclization of α-diazo-β-dithioamides. New rearrangements of 1,2,3,-triazole-4-carbothiamides. Tetrahedron 45:7329–7340 23. Katritzky AR, Ji FB, Fan WQ et al (1992) Novel Dimroth rearrangements of the benzotriazole system: 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles. J Org Chem 57:191–195 24. Temple DH, Smith JA, Montgomery JA (1972) Preparation and properties isomeric v-triazolopyridines. 1- and 3-Deaza-8-azapurines.

1-Sulfonyl-1,2,3-triazoles 163 are also capable of reacting with various nitriles under treatment with rhodium catalyst to form 1,2,4-subsituted imidazoles 164 in high to excellent yields [60] (Scheme 48). Both conventional and microwave heating give the same yield of the final products. A series of rhodium catalysts was examined and both rhodium(II) octanoate and Rh2(S-DOSP)4 were found to be the best. The reaction is found to be general with respect to triazole and nitrile components. Similarly to the reaction of triazolopyridine 161, the transformation of triazoles 163 is regioselective, forming only imidazole type products 164.

Triazoles 4–6 with unsubstituted ring nitrogen atom have special interest due to their importance for the synthesis of new derivatives. NH-triazoles 4–6 are thermodynamically stable tautomers. They exist in equilibrium in solutions and have very close values of Gibbs energy [1, 2, 6–12]. The ratio of tautomeric forms 4–6 can be determined by spectral methods, although it is impossible to separate them. In modern books it is a common practice not to put a certain form of tautomer to represent NH-1,2,3-triazoles, but rather to use generalized formulas, for example 7 or 10.

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