Facile synthetic entry into rotationally restricted 9-arylacridines

Abstract: The treatment of 2-(trifluoromethyl) aniline with 2,6-dimethylphenylmagnesium bromide yields 1-methyl-9-(2,6-dimethylphenyl) acridine by the formal reaction of one equivalent of the aniline and two equivalents of the Grignard reagent. Interestingly, one of the methyl groups is eliminated during the reaction, and the product contains three methyl groups only. In a similar way, the reaction of 2-(trifluoromethyl) aniline with 2-ethylphenylmagnesium bromide furnishes 9-(2-ethylphenyl) acridine devoid of one ethyl group. The mechanism is discussed.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Facile synthetic entry into rotationally restricted 9-arylacridines ; volume:19 ; number:4 ; year:2013 ; pages:245-247
Heterocyclic communications ; 19, Heft 4 (2013), 245-247

Creator
Zhang, Jianguo
Sączewski, Jarosław
Wolińska, Ewa
Strekowski, Lucjan

DOI
10.1515/hc-2013-0106
URN
urn:nbn:de:101:1-2501130544166.386744835088
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:28 AM CEST

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Associated

  • Zhang, Jianguo
  • Sączewski, Jarosław
  • Wolińska, Ewa
  • Strekowski, Lucjan

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