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Synthesis of thienodolin
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
2004 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 12, 2589-2592 p.Article in journal (Refereed) Published
Abstract [en]

We report a total synthesis of the alkaloid thienodolin (1a), as well as its 5-chloro isomer 1b and its unsubstituted analogue 1c, in three steps from the corresponding oxindoles Ba-c. The preparation was achieved through an initial Vilsmeier-Haack-Arnold reaction (chloro-formylation) followed by protection at the indole nitrogen, creation of the fused thiophene ring by nucleophilic substitution at the 2-position and an intramolecular cyclization using mercaptoacetamide. This gave 1a, 1b and 1c in total yields of 42%, 35% and 37%, respectively.

Place, publisher, year, edition, pages
2004. no 12, 2589-2592 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:sh:diva-15474DOI: 10.1002/ejoc.200400073ISI: 000222295800007ScopusID: 2-s2.0-4544251222OAI: oai:DiVA.org:sh-15474DiVA: diva2:504676
Available from: 2012-02-21 Created: 2012-02-20 Last updated: 2017-02-14Bibliographically approved
In thesis
1. Syntheses of some tri- and tetracyclic heterocycles containing an indole moiety
Open this publication in new window or tab >>Syntheses of some tri- and tetracyclic heterocycles containing an indole moiety
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with the development of new synthetic methods leading to fused tri- and tetracyclic heterocycles, many of which have interesting biological activity such as antiviral and DNA intercalating properties. The reactions between isatins and 2-aminobenzylamine in acetic acid can give, depending on the conditions, either complex spirooxindoles or indolo[3,2-c]quinolin-6-ones. Proposed mechanisms are presented (involving a simpler form of spirooxindoles). These spirooxindoles can easily be obtained from isatins and 2-aminobenzylamine in methanol (Paper I). The previously unknown, but incorrectly claimed, linear isomer of indolo[3,2-c]quinolin-6one, i.e. indolo[2,3-b]quinolin-11-one, has been prepared for the first time by thermal (260 degrees C) cyclization of methyl 2 -phenylamino-indole-3 -carboxylate, which was in turn prepared in two steps from methyl indole-3 -carboxylate. The benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one could be prepared similarly (Papers I and II). Suitable 2-chloro-3-formylindoles have been used for the preparation of the alkaloids neocryptolepine, thienodolin and derivatives thereof (Papers III and IV). Finally, synthetic work towards potential metabolites of the lead compound B-220 is presented. We have described a method for reduction of the biologically interesting indolo[2,3b)quinoxalines with zinc, which are subsequently trapped with an appropriate anhydride to provide the corresponding mono or diacylated 5,1 1-dihydroindolo[2,3b]quinoxalines in good yields (paper V). Synthesis of hydroxy derivatives of B-220 can be effected from the appropriate methoxyisatins. Futher derivatives like the vinyl-, Nmethylaminoethyl- and Noxido derivatives of B-220 have also been synthesised.

Place, publisher, year, edition, pages
Stockholm: Karolinska instiutet, 2004. 50 p.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-32058 (URN)91-7140-161-X (ISBN)
Public defence
2004-12-10, Hörsalen, plan 4, NOVUM, Hälsovägen 7-9, Huddinge, 10:00 (English)
Opponent
Supervisors
Available from: 2017-02-14 Created: 2017-02-14 Last updated: 2017-02-14Bibliographically approved

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