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Phase-transfer catalyzed alkylation of pyrazoles and 1,2,4-triazole with cis- and trans-1,4-dichloro-2-butenes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The phase-transfer catalyzed (PTC) alkylation of pyrazoles and 1,2,4-triazole with cis- and trans-1,4-dichloro-2-butenes (DCB) has been examined. The monoalkylation products of pyrazoles with cis-DCB are bicyclic salts formed by intramolecular cyclization of the intermediate cis-1-(4-chloro-2-butenyl)pyrazoles. The corresponding trans-compounds are incapable of cyclization, but on prolonged standing they undergo intermolecular polyquaternization. Both cis- and trans-DCB undergo phase-transfer catalyzed reaction with 1,2,4-triazole to give polymeric quaternary salts. Conditions have been worked out for the dehydrochlorination of 1-(4-chloro-2-butenyl)azoles to 1-(butadien-2-yl)azoles.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Armenian SSR, 375094, Erevan

    O. S. Attaryan, G. V. Asratyan, G. A. éliazyan, G. A. Panosyan, F. S. Kinoyan & E. G. Darbinyan

Authors
  1. O. S. Attaryan
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  2. G. V. Asratyan
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  3. G. A. éliazyan
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  4. G. A. Panosyan
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  5. F. S. Kinoyan
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  6. E. G. Darbinyan
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 497–503, April, 1989.

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Attaryan, O.S., Asratyan, G.V., éliazyan, G.A. et al. Phase-transfer catalyzed alkylation of pyrazoles and 1,2,4-triazole with cis- and trans-1,4-dichloro-2-butenes. Chem Heterocycl Compd 25, 414–420 (1989). https://doi.org/10.1007/BF00480755

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  • DOI: https://doi.org/10.1007/BF00480755

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