REARRANGEMENT OF THIAZOLO[3,2-<i>a</i>]PYRIMIDINES INTO TRIAZOLO[4,3-<i>a</i>]PYRIMIDINES INDUCED BY C=N BOND REDUCTION

Authors

  • Eugenia A. Lashmanova Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Artem S. Agarkov Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Victor B. Rybakov Moscow M. V. Lomonosov State University, 1 Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Andrey K. Shiryaev Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

DOI:

https://doi.org/10.1007/5149

Keywords:

hydrazine derivatives, 2-hydrazinylidene-5H-[1, 3]thiazolo[3, 2-a]pyrimidin-3(2H)-one, [1, 2-a]pyrimidine, 2, 4]triazolo[4, 3-a]pyrimidine, rearrangement, reduction, transition cage structure.

Abstract

Triazolo[4,3-a]pyrimidines were prepared by the reduction of 5,6,7-trisubstituted 2-(arylhydrazinylidene)-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with NaBH4 in the presence of V2O5 at room temperature. The structure of ethyl 3-(hydroxymethyl)-5-(4-methoxyphenyl)-7-methyl-1-phenyl-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate was proven by the single crystal X-ray diffraction data. The mechanism of the reaction including transition cage structure is discussed.

Author Biographies

Eugenia A. Lashmanova, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

Chemistry Dept, Professor

Artem S. Agarkov, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

Chemistry Dept, Assistent

Victor B. Rybakov, Moscow M. V. Lomonosov State University, 1 Build. 3 Leninskie Gory, Moscow 119991, Russia

Chemistry Dept, Student

Andrey K. Shiryaev, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

Chemistry Dept, Senior Scientist

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Published

2019-12-18

Issue

Vol. 55 No. 12 (2019)

Section

Original Papers