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

Sackus, A. ; Valaityte, E. ; Amankaviciene, V. ; Berg, Ulf LU ; Schichktanz, C. and Schlothauer, K. (2007) In Himiâ Geterocikliceskih Soedinenij p.1322-1327
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.
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
13-methano-1, 3-benzoxazepino[3, 5a, 2-a]indoles. spiropyrans, carbanions, cyclization
in
Himiâ Geterocikliceskih Soedinenij
issue
9
pages
1322 - 1327
publisher
Khimiya Geterotsiklicheskikh Soedineniya
external identifiers
  • wos:000251731900003
  • scopus:36348944569
ISSN
0132-6244
language
Russian
LU publication?
yes
additional info
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)
id
3f1b4613-0a1f-43a6-b35c-5bc729d76f24 (old id 1407679)
date added to LUP
2016-04-01 16:40:15
date last changed
2022-03-22 20:19:56
@article{3f1b4613-0a1f-43a6-b35c-5bc729d76f24,
  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.}},
  author       = {{Sackus, A. and Valaityte, E. and Amankaviciene, V. and Berg, Ulf and Schichktanz, C. and Schlothauer, K.}},
  issn         = {{0132-6244}},
  keywords     = {{13-methano-1; 3-benzoxazepino[3; 5a; 2-a]indoles. spiropyrans; carbanions; cyclization}},
  language     = {{rus}},
  number       = {{9}},
  pages        = {{1322--1327}},
  publisher    = {{Khimiya Geterotsiklicheskikh Soedineniya}},
  series       = {{Himiâ Geterocikliceskih Soedinenij}},
  title        = {{Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group}},
  year         = {{2007}},
}