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

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Author

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

Summary, in English

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.

Publishing year

2007

Language

Russian

Pages

1322-1327

Publication/Series

Himiâ Geterocikliceskih Soedinenij

Issue

9

Document type

Journal article

Publisher

Khimiya Geterotsiklicheskikh Soedineniya

Topic

  • Organic Chemistry

Keywords

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

Status

Published

ISBN/ISSN/Other

  • ISSN: 0132-6244