Change search
ReferencesLink to record
Permanent link

Direct link
Bisindoles: synthesis and reactions
KTH, Superseded Departments, Chemistry.
1999 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

In this thesis, synthesis of various bisindoles have beendeveloped.2,3-Bis-(3-indolyl) succinic acid derivatives wereobtained via iodine promoted coupling of the trianion ofindole-3-acetic acid (IAA) or from the dianion of themethylester of IAA. These compounds were converted to2,3-bis(3-indolyl) maleimides (arcyriarubin analogues) by DDQoxidation. Indolo[2,3-a]carbazoles were obtained by DDQ promoted cyclization/dehydrogenation orviaacid induced cyclization in TFA. Some of thesecompounds were obtained in an isomerically pure form and theirstructures were determined.Indolo[3,2-a]carbazoles were synthesized in one-step from indoleand various maleimides. The mechanism of the reaction isdiscussed.3,3’-Disubstituted 2,2’-biindolyls have beensynthesized from 2,2’-biindolyl by substitution reactionsand by dimerization of IAA and esters of IAA.2:2 Condensation products are obtained when2,2’-biindolyl is reacted with various benzaldehydes,forming ten-membered rings.A bisindole structure containing a cyclopentano ringfused to theb-face of one of the indoles is formed in an acidinduced dimerization/cyclization tandem reaction ofN-benzyl-3-(3-indolyl)maleimide.The synthetic concept which primarily have been utilizedin the synthesic work described here is acid induceddimerization and/or cyclization of an intermediate indoliumion.

Keywords:bisindoles, acid-induceddimerization/cyclization, oxidative coupling, indolium ion,indolo[2,3-a]carbazole, indolo[3,2-a]carbazole, 2,2’-biindolyl.

Place, publisher, year, edition, pages
Stockholm: Kemi , 1999. , 46 p.
Trita-IOK, ISSN 1100-7974 ; 53
URN: urn:nbn:se:kth:diva-2773ISBN: 99-2920220-XOAI: diva2:8485
Public defence
NR 20140805Available from: 2000-01-01 Created: 2000-01-01Bibliographically approved

Open Access in DiVA

fulltext(437 kB)1262 downloads
File information
File name FULLTEXT01.pdfFile size 437 kBChecksum SHA-1
Type fulltextMimetype application/pdf

By organisation

Search outside of DiVA

GoogleGoogle Scholar
Total: 1262 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Total: 593 hits
ReferencesLink to record
Permanent link

Direct link