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Reduction of indolo[2,3-b]quinoxalines
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
AstraZeneca.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
2005 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 61, no 18, 4495-4500 p.Article in journal (Refereed) Published
Abstract [en]

Reduction of indolo[2,3-b]quinoxalines with zinc in the presence of an anhydride gave N,N-diacyl trapped 6,11-dihydroindolo[2,3-b]quinoxalines in 43-92% yields. When the reduction with zinc was performed in TFA/TFAA, an unexpected ring opened product was isolated in 49% yield. The structure of this product could be identified as 1,2-dihydro-1-trifluoroacetyl-3-[(2-trifluoroacetylamino)phenyl]quinoxal ine.

Place, publisher, year, edition, pages
2005. Vol. 61, no 18, 4495-4500 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:sh:diva-14382DOI: 10.1016/j.tet.2005.02.060ISI: 000228607400018ScopusID: 2-s2.0-17044402179OAI: oai:DiVA.org:sh-14382DiVA: diva2:469159
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2011-12-22 Created: 2011-12-21 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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