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Russian Chemical Bulletin

, Volume 44, Issue 11, pp 2114–2117 | Cite as

Acylation of spiro(1-pyrazoline-3,1′-cyclopropanes) to form 1-acyl-3-(2-chloroethyl)-2-pyrazolines and transformation of bicyclic 2-pyrazolines into 1,4,5,6-tetrahydropyridazines

  • Yu. V. Tomilov
  • G. P. Okonnishnikova
  • E. V. Shulishov
  • O. M. Nefedov
Organic Chemistry

Abstract

Strained polycyclic spiro(1-pyrazoline-3,1′-cyclopropanes) react with acetyl or benzoyl chlorides at 0–15 °C regioselectively to give in high yields corresponding 1-acyl-3-(2-chloro-ethyl)-2-pyrazolines. Under the same conditions 6-ethenyl-4,5-diazaspiro[2,4]hept-4-ene gives a mixture of two pyrazolines resulting from the acyl group attack directed at different nitrogen atoms. Bicyclic pyrazolines-2 obtained by acylation of the cycloaddition products of diazocyclopropane with 3,3-disubstituted cyclopropenes transform under the action of hydrogen chloride to 1,4,5,6-tetrahydropyridazines in high yields.

Key words

spiro(1-pyrazolines-1,3′-cyclopropane) 2,3-diazabicyclo[3.1,0]hex-3-enes 1,4,5,6-tetrahydropyridazines acylation reaction opening of cyclopropane ring 

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Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • Yu. V. Tomilov
    • 1
  • G. P. Okonnishnikova
    • 1
  • E. V. Shulishov
    • 1
  • O. M. Nefedov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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