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Benzimidazoles and related heterocycles

8. Acid-catalyzed rearrangement of 3-aryl-1’H-spiro[2-pyrazoline-5,2’-quinoxalin]-3’(4’H)-ones as a new efficient method for the synthesis of 2-(pyrazol-3-yl)benzimidazoles

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Abstract

3-Aryl-1’H-spiro[2-pyrazoline-5,2’-quinoxalin]-3’(4’H)-ones, easily available by the reaction of 3-(2-aryl-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones with hydrazine hydrate (and phenylhydrazine), in boiling acetic acid undergo new acid-catalyzed rearrangement with the contraction of pyrazine ring of the quinoxaline system to form 2-(pyrazol-3-yl)benzimidazoles. Possible mechanisms of this rearrangement are considered.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. A. Mamedov, A. M. Murtazina, A. T. Gubaidullin, E. A. Khafizova, I. Kh. Rizvanov & I. A. Litvinov

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  1. V. A. Mamedov
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  2. A. M. Murtazina
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  3. A. T. Gubaidullin
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  4. E. A. Khafizova
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  5. I. Kh. Rizvanov
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  6. I. A. Litvinov
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Corresponding author

Correspondence to V. A. Mamedov.

Additional information

For Parts 1–7, see Refs 1–7.

Dedicated to Professor I. A. Nuretdinov on his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1602–1611, August, 2010.

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Mamedov, V.A., Murtazina, A.M., Gubaidullin, A.T. et al. Benzimidazoles and related heterocycles. Russ Chem Bull 59, 1645–1655 (2010). https://doi.org/10.1007/s11172-010-0289-7

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  • DOI: https://doi.org/10.1007/s11172-010-0289-7

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