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Synthesis of imidazo[4,5-e]-2,1,3-benzoselenadiazoles and derivatives thereof
Södertörns högskola, Institutionen för livsvetenskaper. Karolinska Institutet.
Södertörns högskola, Institutionen för livsvetenskaper. Karolinska Institutet.
(engelsk)Manuskript (preprint) (Annet vitenskapelig)
HSV kategori
Identifikatorer
URN: urn:nbn:se:sh:diva-31998OAI: oai:DiVA.org:sh-31998DiVA, id: diva2:1072808
Merknad

Som manuskript i avhandling. As manuscript in dissertation.

Tilgjengelig fra: 2017-02-08 Laget: 2017-02-08 Sist oppdatert: 2025-10-07bibliografisk kontrollert
Inngår i avhandling
1. Synthesis of sulfur and seleniumn heterocycles, including derivatives of imidazopyridine and benzimidazole
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis of sulfur and seleniumn heterocycles, including derivatives of imidazopyridine and benzimidazole
2005 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The chemistry developed in this thesis can be divided into two parts. The first part, which is the major part of the thesis, contains syntheses towards analogues to mutagenic heterocyclic amines found in e.g. meat fried at high temperatures. The second part concentrates on the palladium-(0)catalyzed cross-coupling reactions of 4- and 5-substituted 2,1,3-benzoselenadiazoles. The heterocyclic amines described can be divided into the linear and the angular compounds. Five linear imidazo[4,5-b]pyridines were synthesised via the Friedländer reaction: 2-amino-1 - methylbenzothieno[2,3-e]imidazo[4,5-b]pyridine, 2-amino-1-methy-benzothieno [3,2-e] imidazo[4,5-b] pyridine, 2-amino-1-methylthieno[2,3-elimidazo[4,5-b]-pyridine, 2-amino-1methylthieno[3,2-e]imidazo[4,5-b]pyridine and the sulfur analogue to the cooked-food mutagen IFP, 2-amino- 1,6-dimethylthieno[2,3-e]imidazo[4,5-b]pyridine. Attempts were made to form three thienoimidazo[4,5-b]pyridines via stepwise condensation. The first condensation between creatinine and 2-nitro-3-thiophene-carbaldehyde, 3-amino-2thiophenecarbaldehyde and 4-azido3-thiophenecarbaldehyde yielded thenylidenomethyleneimidazolinones, but only one of these gave the ring closed compound 2-amino-1-methylthieno[2,3-e]imidazo[4,5-b]pyridine by a second condensation. In addition, 2-amino- 1 methyl benzoth ieno[3,2-e] imidazo[4,5 -b] pyridine was transformed into the 2-nitro- and 2-hydroxy derivative. The last linear isomer 2-amino-1methylimidazo[4,5-b]benzothiophene, was synthesized by a different route. The series of angular compounds are considered analogues to the food-mutagen IQx. A series of six homologues of 7-amino-imidazo[4,5-e]-2,1,3-benzoselenadiazoles. Four ring systems were obtained by treating 4-methylamino-3-nitro-phenylenedianmine with a range of biselectrophiles, namely: 2-amino-1-methylbenzo-thiadiazole, -triazole, -diazepinone and 2amino1 -methylimidazobenzimidazole. Among the palladium-(0)-catalyzed cros s- couplings, the Suzuki, Stille, Fleck and Sonogashira reactions were used. These were applied to 4-, or 5-bromo-2,1,3-benzoselenadiazoles. In addition, the 4- and 5-trimethyltin-2,1,3-benzoselenadiazole were synthesized.

sted, utgiver, år, opplag, sider
Stockholm: Karolinska instiutet, 2005. s. 40
HSV kategori
Identifikatorer
urn:nbn:se:sh:diva-32000 (URN)91-7140-597-6 (ISBN)
Disputas
2005-12-15, Hörsalen, plan 4, NOVUM, Hälsovägen 7-9, Huddinge, 10:00 (engelsk)
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Veileder
Tilgjengelig fra: 2017-02-08 Laget: 2017-02-08 Sist oppdatert: 2025-10-07bibliografisk kontrollert

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