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Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
2004 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 16, 2760-2765 p.Article in journal (Refereed) Published
Abstract [en]

Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.

Place, publisher, year, edition, pages
2004. no 16, 2760-2765 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:sh:diva-15459DOI: 10.1055/s-2004-831164ISI: 000225051500029Scopus ID: 2-s2.0-8744311405OAI: oai:DiVA.org:sh-15459DiVA: diva2:504699
Available from: 2012-02-21 Created: 2012-02-20 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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