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Cyclization of nitrospirobenzopyrans to bridged benzoxazepino[3,2-a]indoles

Kleiziene, Neringa ; Amankaviciene, Virgine ; Berg, Ulf LU ; Schicktanz, Carsten ; Schlothauer, Klaus and Sackus, Algirdas (2006) In Monatshefte fur Chemie 137(8). p.1109-1117
Abstract
Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1'-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans. Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system.
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
carbanions, nitrospiropyrans, heterocycles, indoles, 5a, 13-methano-1, 3-benzoxazepino[3, 2-a]indoles
in
Monatshefte fur Chemie
volume
137
issue
8
pages
1109 - 1117
publisher
Springer
external identifiers
  • wos:000240021000015
  • scopus:33746932791
ISSN
1434-4475
DOI
10.1007/s00706-005-0504-7
language
English
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
5ee2192d-1b0b-42fb-95ff-d5c09a414490 (old id 394990)
date added to LUP
2016-04-01 12:01:53
date last changed
2025-10-14 10:35:24
@article{5ee2192d-1b0b-42fb-95ff-d5c09a414490,
  abstract     = {{Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1'-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans. Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system.}},
  author       = {{Kleiziene, Neringa and Amankaviciene, Virgine and Berg, Ulf and Schicktanz, Carsten and Schlothauer, Klaus and Sackus, Algirdas}},
  issn         = {{1434-4475}},
  keywords     = {{carbanions; nitrospiropyrans; heterocycles; indoles; 5a; 13-methano-1; 3-benzoxazepino[3; 2-a]indoles}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{1109--1117}},
  publisher    = {{Springer}},
  series       = {{Monatshefte fur Chemie}},
  title        = {{Cyclization of nitrospirobenzopyrans to bridged benzoxazepino[3,2-a]indoles}},
  url          = {{http://dx.doi.org/10.1007/s00706-005-0504-7}},
  doi          = {{10.1007/s00706-005-0504-7}},
  volume       = {{137}},
  year         = {{2006}},
}