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Syntheses of some tri- and tetracyclic heterocycles containing an indole moiety
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
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: urn:nbn:se:sh:diva-32058ISBN: 91-7140-161-X (print)OAI: oai:DiVA.org:sh-32058DiVA: diva2:1074161
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
List of papers
1. Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
Open this publication in new window or tab >>Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
2003 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 7, 1033-1048 p.Article in journal (Refereed) Published
National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-15639 (URN)10.1016/S0040-4020(02)01647-2 (DOI)000180906000012 ()2-s2.0-0037429056 (Scopus ID)
Available from: 2012-02-23 Created: 2012-02-22 Last updated: 2017-02-14Bibliographically approved
2. Synthesis of benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one
Open this publication in new window or tab >>Synthesis of benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one
2003 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 48, 9649-9653 p.Article in journal (Refereed) Published
Abstract [en]

The fused heterocycles benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one, have been prepared from methyl 3-indole carboxylate in two steps.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:sh:diva-15521 (URN)10.1016/j.tet.2003.09.084 (DOI)000186617600018 ()2-s2.0-0242384131 (Scopus ID)
Available from: 2012-02-21 Created: 2012-02-21 Last updated: 2017-02-14Bibliographically approved
3. An improved synthesis of neocryptolepine
Open this publication in new window or tab >>An improved synthesis of neocryptolepine
2004 (English)In: Organic preparations and procedures international, ISSN 0030-4948, E-ISSN 1945-5453, Vol. 36, no 4, 386-390 p.Article in journal (Refereed) Published
National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-15471 (URN)10.1080/00304940409458686 (DOI)000223630600014 ()2-s2.0-4644277659 (Scopus ID)
Available from: 2012-02-21 Created: 2012-02-20 Last updated: 2017-02-14Bibliographically approved
4. Synthesis of thienodolin
Open this publication in new window or tab >>Synthesis of thienodolin
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.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-15474 (URN)10.1002/ejoc.200400073 (DOI)000222295800007 ()2-s2.0-4544251222 (Scopus ID)
Available from: 2012-02-21 Created: 2012-02-20 Last updated: 2017-02-14Bibliographically approved
5. Reduction of indolo[2,3-b]quinoxalines
Open this publication in new window or tab >>Reduction of indolo[2,3-b]quinoxalines
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.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-14382 (URN)10.1016/j.tet.2005.02.060 (DOI)000228607400018 ()2-s2.0-17044402179 (Scopus ID)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2011-12-22 Created: 2011-12-21 Last updated: 2017-02-14Bibliographically approved

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