Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group

A. Sackus, E. Valaityte, V. Amankaviciene, Ulf Berg, C. Schichktanz, K. Schlothauer

Research output: Contribution to journalArticlepeer-review


Condensation of 1-cyanomethyl-2,3,3-trimethyl-3H-indolium perchlorate with ortho-hydroxy-substituted aromatic aldehydes afforded 1-cyanomethylindoline spiropyrans. The latter underwent rearrangement to bridged 1,3-benzoxazepino[3,2-a]indoles on treatment with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano Group.
Original languageRussian
Pages (from-to)1322-1327
JournalHimiâ Geterocikliceskih Soedinenij
Issue number9
Publication statusPublished - 2007

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

Free keywords

  • 13-methano-1
  • 3-benzoxazepino[3
  • 5a
  • 2-a]indoles. spiropyrans
  • carbanions
  • cyclization

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