TRANSFORMATION OF INDOLINE SPIROPYRANS TO BRIDGED 1,3-BENZOXAZEPINO[3,2-<i>a</i>]INDOLES <i>VIA</i> CARBANIONS STABILIZED BY A CYANO GROUP

Authors

  • A. Šačkus Institute of Synthetic Chemistry, Kaunas University of Technology, Kaunas LT-50254
  • E. Valaitytė Institute of Synthetic Chemistry, Kaunas University of Technology, Kaunas LT-50254
  • V. Amankavičienė Institute of Synthetic Chemistry, Kaunas University of Technology, Kaunas LT-50254
  • U. Berg Organic Chemistry 1, Department of Chemistry, Lund University, 22100 Lund
  • C. Schicktanz Faculty of Informatics and Nature Sciences, University of Applied Sciences, 06217 Merseburg
  • K. Schlothauer Faculty of Informatics and Nature Sciences, University of Applied Sciences, 06217 Merseburg

DOI:

https://doi.org/10.1007/7391

Keywords:

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

Abstract

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.

How to Cite
Šačkus,  A.; Valaitytė, E.; Amankavičienė, V.; Berg, U.; Schicktanz, C.; Schlothauer, K.  Chem. Heterocycl. Compd. 2007, 43, 1118. [Khim. Geterotsikl. Soedin. 2007, 1322.]

For this article in the English edition see DOI 10.1007/s10593-007-0172-0

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Published

2023-01-27

Issue

No. 9 (2007)

Section

Original Papers