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Thionation of bisindole derivatives with P4S10 or elemental sulfur

Janosik, Tomasz; Bergman, Jan; Stensland, Birgitta and Stålhandske, Claes-Ivar LU (2002) In Perkin Transactions 1 p.330-334
Abstract
Thionation reactions of several bisindole derivatives using elemental sulfur or P4S10 in pyridine have been studied, leading to formation of several novel structures. The reaction of indigo or isatin with P4S10 gave the structurally new salt 10, which could be transformed into the ethyl derivative 11. The first example of a thionated indigo derivative, monothioindigo (6), was isolated in low yield from the thionation of isatin. Treatment of 3,3'-biindolyl with sulfur in hot DMF produced the previously known tetrasulfide 1, which was studied by X-ray crystallography, thus also establishing that 1 is chiral in the crystalline state. The structure of an additional thionation product, the thienoindole derivative 34 was also solved using X-ray... (More)
Thionation reactions of several bisindole derivatives using elemental sulfur or P4S10 in pyridine have been studied, leading to formation of several novel structures. The reaction of indigo or isatin with P4S10 gave the structurally new salt 10, which could be transformed into the ethyl derivative 11. The first example of a thionated indigo derivative, monothioindigo (6), was isolated in low yield from the thionation of isatin. Treatment of 3,3'-biindolyl with sulfur in hot DMF produced the previously known tetrasulfide 1, which was studied by X-ray crystallography, thus also establishing that 1 is chiral in the crystalline state. The structure of an additional thionation product, the thienoindole derivative 34 was also solved using X-ray crystallography. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Perkin Transactions 1
issue
3
pages
330 - 334
publisher
Royal Society of Chemistry
external identifiers
  • wos:000173477700008
  • scopus:0036007706
ISSN
1472-7781
DOI
10.1039/b109840c
language
English
LU publication?
yes
id
9009b878-4777-44b2-ab0e-55152fefe7b9 (old id 344406)
date added to LUP
2007-10-24 13:36:40
date last changed
2017-11-12 04:04:43
@article{9009b878-4777-44b2-ab0e-55152fefe7b9,
  abstract     = {Thionation reactions of several bisindole derivatives using elemental sulfur or P4S10 in pyridine have been studied, leading to formation of several novel structures. The reaction of indigo or isatin with P4S10 gave the structurally new salt 10, which could be transformed into the ethyl derivative 11. The first example of a thionated indigo derivative, monothioindigo (6), was isolated in low yield from the thionation of isatin. Treatment of 3,3'-biindolyl with sulfur in hot DMF produced the previously known tetrasulfide 1, which was studied by X-ray crystallography, thus also establishing that 1 is chiral in the crystalline state. The structure of an additional thionation product, the thienoindole derivative 34 was also solved using X-ray crystallography.},
  author       = {Janosik, Tomasz and Bergman, Jan and Stensland, Birgitta and Stålhandske, Claes-Ivar},
  issn         = {1472-7781},
  language     = {eng},
  number       = {3},
  pages        = {330--334},
  publisher    = {Royal Society of Chemistry},
  series       = {Perkin Transactions 1},
  title        = {Thionation of bisindole derivatives with P4S10 or elemental sulfur},
  url          = {http://dx.doi.org/10.1039/b109840c},
  year         = {2002},
}