Russian Journal of Organic Chemistry

, Volume 45, Issue 7, pp 1040–1044 | Cite as

Synthesis and reactions of pyrazole-4-carbaldehydes

  • E. V. Rudyakova
  • V. A. Savosik
  • L. K. Papernaya
  • A. I. Albanov
  • I. T. Evstaf’eva
  • G. G. Levkovskaya
Article

Abstract

1-, 3-, and 5-Alkylpyrazoles, as well as linearly bridged bis-pyrazoles, were converted into the corresponding 4-formyl derivatives by Vilsmeier-Haak reaction both under standard conditions and under microwave activation in DMF over a period of 10 min. 1,1′-(Hexane-1,6-diyl)bis(3,5-dimethyl-1H-pyrazole) and 1,1′-(benzene-1,4-diyldimethylene)bis(3,5-dimethyl-1H-pyrazole) gave rise to 4-formyl derivatives at both pyrazole rings. 5-Chloro-1,3-dialkyl-1H-pyrazoles failed to undergo formylation according to Vilsmeier-Haak or under microwave activation. 1,1′-Bridged bis-3,5-dimethyl-1H-pyrazoles reacted with 2-sulfanylethanol on heating in the presence of chloro(trimethyl)silane to give the corresponding bridged bis-4-(1,4,6-oxadithiocan-5-yl)-1H-pyrazoles.

Keywords

Pyrazole Pyrazole Ring Microwave Activation Sodium Hydrogen Carbonate Phosphoryl Chloride 

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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • E. V. Rudyakova
    • 1
  • V. A. Savosik
    • 1
  • L. K. Papernaya
    • 1
  • A. I. Albanov
    • 1
  • I. T. Evstaf’eva
    • 1
  • G. G. Levkovskaya
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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