Synthesis of 2-(9H-carbazol-1-yl)anilines from 2,3′-biindolyl and ketones

Wayland E. Noland, Christopher D. Brown, Abigail E. Zabronsky, Kenneth J. Tritch

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Twenty-nine examples of 2-(9H-carbazol-1-yl)anilines were obtained in yields from 27 to 95% by refluxing 2,3′-biindolyl (1 equiv.) and ketones (1 equiv.) in ethanolic HCl. Alkyl, cyclic, and aryl ketones were found to be compatible with this method, however, aldehydes are not. Because the reaction proceeds by addition of the carbonyl C atom to the biindolyl 3-position, this method has high regioselectivity. One example is presented of bridging the two N atoms in the carbazolylaniline product with an acetaldehyde synthon to give a benzodiazepino[lm]carbazole. Also, one example is given of installing a dimethylamino group at the α-position of the starting ketone to give an indolo[3,2-c]carbazole.

Original languageEnglish (US)
Pages (from-to)2391-2404
Number of pages14
JournalTetrahedron
Volume74
Issue number19
DOIs
StatePublished - May 10 2018

Bibliographical note

Funding Information:
The authors thank undergraduate research assistants, Mark A. Mills and Janel L. Rieger, for preparing several batches of compound 3 , and Andrew K. Schneerer for assistance in the synthesis and isolation of compound 24 . The authors also thank the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for the financial support of this project.

Publisher Copyright:
© 2018 Elsevier Ltd

Keywords

  • 2,3′-biindolyl
  • Cyclizative condensation
  • Ketones
  • Metal-free
  • Substituted carbazoles

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