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Oxygenation of 2,3-dihydroindoles
Södertörns högskola, Avdelning Naturvetenskap. Karolinska Institutet.
Södertörns högskola, Avdelning Naturvetenskap. Karolinska Institutet.
2002 (Engelska)Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, nr 45, s. 9187-9191Artikel i tidskrift (Refereegranskat) 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).

Ort, förlag, år, upplaga, sidor
2002. Vol. 58, nr 45, s. 9187-9191
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:sh:diva-15774DOI: 10.1016/S0040-4020(02)01198-5ISI: 000179069000005Scopus ID: 2-s2.0-0037020798OAI: oai:DiVA.org:sh-15774DiVA, id: diva2:508480
Tillgänglig från: 2012-03-08 Skapad: 2012-03-07 Senast uppdaterad: 2025-10-07Bibliografiskt granskad
Ingår i avhandling
1. Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
Öppna denna publikation i ny flik eller fönster >>Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
2005 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: Karolinska instiutet, 2005. s. 39
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:sh:diva-31953 (URN)91-7140-269-1 (ISBN)
Disputation
2005-03-18, 4U, Alfred Nobels allé, Huddinge, 10:00 (Engelska)
Opponent
Handledare
Tillgänglig från: 2017-02-06 Skapad: 2017-02-06 Senast uppdaterad: 2025-10-07Bibliografiskt granskad

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