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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 11, pp 1124–1127 | Cite as

Preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines by a one-step reaction of 1,2,4-triazines with 1,2-dehydrobenzene

  • Igor L. Nikonov
  • Pavel A. Slepukhin
  • Dmitry S. Kopchuk
  • Igor S. Kovalev
  • Grigory V. ZyryanovEmail author
  • Anna I. Suvorova
  • Oleg S. Eltsov
  • Vladimir L. Rusinov
  • Oleg N. Chupakhin
Article
  • 13 Downloads

An original and convenient procedure has been proposed for one-step preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines in up to 40% yields via aza-Diels–Alder reaction of the readily available 3-dichloromethyl- and 3-trichloromethyl-1,2,4-triazines (in the role of dienes) with 1,2-dehydrobenzene (in the role of in situ generated dienophile). The structure of 1-trichloromethyl-4-phenylisoquinoline was confirmed by X-ray structural analysis.

Keywords

aryne intermediates 1-dichloromethylisoquinolines 1,2,4-triazines 1-trichloromethylisoquinolines aza-Diels–Alder reaction X-ray structural analysis 

Notes

This work received financial support from the Russian Science Foundation (grant 18-13-00365).

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Igor L. Nikonov
    • 1
    • 2
  • Pavel A. Slepukhin
    • 1
    • 2
  • Dmitry S. Kopchuk
    • 1
    • 2
  • Igor S. Kovalev
    • 1
  • Grigory V. Zyryanov
    • 1
    • 2
    Email author
  • Anna I. Suvorova
    • 1
  • Oleg S. Eltsov
    • 1
  • Vladimir L. Rusinov
    • 1
    • 2
  • Oleg N. Chupakhin
    • 1
    • 2
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia

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