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The cyclopropyliminium rearrangement of 2-cyclopropyl-4-nitrobenzimidazoles

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Abstract

2-Cyclopropyl-4(7)-nitrobenzimidazoles undergo the cyclopropyliminium rearrangement into two isomeric 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles, one isomer considerably dominating over the other. This reaction is more regioselective than those involving 5- or 6-substituted analogs, which is due to the electronic and steric effects of the nitro group as well as to stabilization of one intermediate by hydrogen bonding between the adjacent NH and NO2 fragments.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    R. F. Salikov, D. N. Platonov, D. L. Lipilin, A. E. Frumkin & Yu. V. Tomilov

Authors
  1. R. F. Salikov
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  2. D. N. Platonov
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  3. D. L. Lipilin
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  4. A. E. Frumkin
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  5. Yu. V. Tomilov
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Corresponding author

Correspondence to Yu. V. Tomilov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0765–0769, March, 2014.

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Salikov, R.F., Platonov, D.N., Lipilin, D.L. et al. The cyclopropyliminium rearrangement of 2-cyclopropyl-4-nitrobenzimidazoles. Russ Chem Bull 63, 765–769 (2014). https://doi.org/10.1007/s11172-014-0505-y

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  • DOI: https://doi.org/10.1007/s11172-014-0505-y

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