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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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