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Oxygenation of 2,3-dihydroindoles
Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
2002 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 45, 9187-9191 p.Article in journal (Refereed) Published
Abstract [en]

Isatogens (3-oxo-3H-indole 1-oxides) possess interesting biological properties and development of a general method to construct these derivatives has now been developed. Indolines (2,3-dihydroindoles) and isatogens have been prepared in an efficient route starting from indoles substituted in position 2. Reduction of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic acid (m-CPBA).

Place, publisher, year, edition, pages
2002. Vol. 58, no 45, 9187-9191 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:sh:diva-15774DOI: 10.1016/S0040-4020(02)01198-5ISI: 000179069000005ScopusID: 2-s2.0-0037020798OAI: oai:DiVA.org:sh-15774DiVA: diva2:508480
Available from: 2012-03-08 Created: 2012-03-07 Last updated: 2017-02-06Bibliographically approved
In thesis
1. Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
Open this publication in new window or tab >>Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is based on an organic synthetic project aimed towards development of small molecules acting on the P2 receptor as well as development of synthetic methods to such molecules (primarily indoles and featuring isatogens in particular). The new methodology includes cyanoacetylation of indoles, pyrroles, amines, and enamines using cyanoacetic acid in acetic anhydride. The molecules obtained (e.g. 3-cyanoacetylindole) could be further functionalized by nitrosation followed by reduction. Cyanoacetylated anilines carrying an appropriate substituent (e.g NO2) could be cyclized to quinoxaline-N-oxides, a class of molecules which have been considered as analogues to isatogens. The molecule 2,2'-pyridylisatogen tosylate (PIT) is particularly interesting within this class because of its documented interaction with the P2 receptor.

Place, publisher, year, edition, pages
Stockholm: Karolinska instiutet, 2005. 39 p.
National Category
Chemical Sciences
Identifiers
urn:nbn:se:sh:diva-31953 (URN)91-7140-269-1 (ISBN)
Public defence
2005-03-18, 4U, Alfred Nobels allé, Huddinge, 10:00 (English)
Opponent
Supervisors
Available from: 2017-02-06 Created: 2017-02-06 Last updated: 2017-02-06Bibliographically approved

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