Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

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

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.

This is a preview of subscription content, log in to check access.

References

  1. 1.

    Yu. V. Tomilov, G. P. Okonnishnikova, E. V. Shulishov, and O. M. Nefedov,Mendeleev Commun., 1994, 119.

  2. 2.

    Yu. V. Tomilov, G. P. Okonnishnikova, E. V. Shulishov, and O. M. Nefedov,Izv. Akad. Nauk, Ser. Khim., 1994, 1993 [Russ. Chem. Bull., 1994,43, 1880 (Engl. Transl.)].

  3. 3.

    Yu. V. Tomilov, E. V. Shulishov, G. P. Okonnishnikova, and O. M. Nefedov,Izv. Akad. Nauk, Ser. Khim., 1995, 2199 [Russ. Chem. Bull., 1995,44, 2105 (Engl. Transl.)].

  4. 4.

    M. I. Komendantov, R. R. Bekmukhamedov, and V. G. Novitsky,Zh. Org. Khim., 1967,12, 801 [J. Org. Chem., 1967,12 (Engl. Transl.)].

  5. 5.

    M. Franck-Neumann and C. Buchecker,Tetrahedron Lett., 1969, 2659.

  6. 6.

    C. H. Jarboe, inThe Chemistry of Heterocyctic Compounds, Ed. A. Weissberger, Wiley, 1967,22, 209.

Download references

Author information

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2208–2211, November, 1995.

The work was carried out with financial support of the Russian Foundation for Basic Research (Grant No. 94-03-08902).

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Tomilov, Y.V., Okonnishnikova, G.P., Shulishov, E.V. et al. 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. Russ Chem Bull 44, 2114–2117 (1995). https://doi.org/10.1007/BF00696715

Download citation

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