Russian Journal of Organic Chemistry

, Volume 43, Issue 2, pp 231–240 | Cite as

Thermal and acid-catalyzed transformations of 3H-pyrazoles obtained from diphenyldiazomethane and methyl phenylpropiolate

  • A. A. Fedorov
  • Sh. E. Duisenbaev
  • V. V. Razin
  • M. A. Kuznetsov
  • E. Linden


Reaction of diphenyldiazomethane with methyl phenylpropiolate in diethyl ether alongside the expected methyl triphenyl-3H-pyrazole-4-and-5-carboxylates (I and II) (38 and 24%) gave rise also to 8% of methyl 3,5-diphenyl-1-(1-ethoxyethyl)-1H-pyrazole-4-carboxylate. The main thermolysis product obtained from 4-methoxy-carbonyl derivative I was methyl 1,3,5-triphenyl-1H-pyrazole-4-carboxylate, whereas from regioisomer II formed predominantly methyl 4,4,5-triphenyl-4H-pyrazole-3-carboxylate and 1-methoxycarbonyl-2,3,3-triphenylcyclopropene that was a minor product of 3H-pyrazole I thermolysis. Addition of concn. H2SO4 to the solutions of methyl triphenyl-3H-pyrazole-4-and-5-carboxylates in AcOH resulted in fast regioselective isomerization of the 3H-pyrazole derivatives into the corresponding 4H-pyrazoles.


Pyrazole Azole Thermolysis Thermolysis Product Anhydrous Ethyl Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • A. A. Fedorov
    • 1
  • Sh. E. Duisenbaev
    • 1
  • V. V. Razin
    • 1
  • M. A. Kuznetsov
    • 1
  • E. Linden
    • 2
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut fur Organische ChemieUniversitat ZurichZurichSwitzerland

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