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Synthetic applications of 3-(cyanoacetyl)indoles and related compounds
Södertörns högskola, Institutionen för kemi, biologi, geografi och miljövetenskap. Karolinska Institutet.
Södertörns högskola, Institutionen för kemi, biologi, geografi och miljövetenskap. Karolinska Institutet.
Södertörns högskola, Institutionen för kemi, biologi, geografi och miljövetenskap. Karolinska Institutet.
Södertörns högskola, Institutionen för kemi, biologi, geografi och miljövetenskap. Karolinska Institutet.
2005 (engelsk)Inngår i: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 42, nr 1, s. 141-145Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Various synthetic applications of 3-(cyanoacetyl)indoles, as well as syntheses of some related indoles, have been investigated. Diethyl 2-(1H-indol-3-yl)-2-oxoethylphosphonate and a methyl derivative thereof have been prepared in one step from indole. Moreover, it was demonstrated that 3-(cyanoacetyl)indoles are useful starting materials for the preparation of for example 3-(1H-indol-3-yl)-3-oxopropanamides, 3-heteroarylindoles or 3-heteroaroylindoles.

sted, utgiver, år, opplag, sider
2005. Vol. 42, nr 1, s. 141-145
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Identifikatorer
URN: urn:nbn:se:sh:diva-14397DOI: 10.1002/jhet.5570420122ISI: 000227157500022Scopus ID: 2-s2.0-17844400315OAI: oai:DiVA.org:sh-14397DiVA, id: diva2:468860
Merknad

Som manuskript i avhandling. As manuscript in dissertation.

Tilgjengelig fra: 2011-12-21 Laget: 2011-12-21 Sist oppdatert: 2025-10-07bibliografisk kontrollert
Inngår i avhandling
1. Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
Åpne denne publikasjonen i ny fane eller vindu >>Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
2005 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: Karolinska instiutet, 2005. s. 39
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Identifikatorer
urn:nbn:se:sh:diva-31953 (URN)91-7140-269-1 (ISBN)
Disputas
2005-03-18, 4U, Alfred Nobels allé, Huddinge, 10:00 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2017-02-06 Laget: 2017-02-06 Sist oppdatert: 2025-10-07bibliografisk kontrollert

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