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Synthesis of sulfur and seleniumn heterocycles, including derivatives of imidazopyridine and benzimidazole
Södertörn University, School of Life Sciences. Karolinska Institutet.
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
Stockholm: Karolinska instiutet , 2005. , 40 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:sh:diva-32000ISBN: 91-7140-597-6 (print)OAI: oai:DiVA.org:sh-32000DiVA: diva2:1072812
Public defence
2005-12-15, Hörsalen, plan 4, NOVUM, Hälsovägen 7-9, Huddinge, 10:00 (English)
Opponent
Supervisors
Available from: 2017-02-08 Created: 2017-02-08 Last updated: 2017-02-08Bibliographically approved
List of papers
1. Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP
Open this publication in new window or tab >>Synthesis of novel 2-aminoimidazo[4,5-b]pyridines, including the thieno analogue of the cooked-food mutagen IFP
2006 (English)In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 43, no 1, 101-109 p.Article in journal (Refereed) Published
Abstract [en]

Eight new compounds, including three new ring systems obtained via the Friedlander condensation of ortho-aminothiophenecarbaldehydes 11, 21 and 24 with creatinine (8), are reported. The condensation afforded 1, which is the thieno analogue of the cooked-food mutagen IFP (2-amino-1,6-dimethylfuro[2,3-e]imidazo[4,5-b]pyridine), and the benzothieno[2,3-e]- and benzothieno[3,2-e]imidazo[4,5-b]pyridines 2 and 3. Attempts to condense 11 with isocreatinine (12) were unsuccessful. Desulfurization of 3 gave the known cooked-food carcinogen PhIP. The 2-nitro (4) and 2-hydroxy (5) derivatives of 3 are reported. The related 2-amino-1-methyl-imidazo[4,5-b]benzothiophene (25) was synthesized by a different route. Fully assigned H-1 and C-13 nmr data of all new compounds are reported.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-14317 (URN)10.1002/jhet.5570430116 (DOI)000234531100016 ()2-s2.0-30844448805 (Scopus ID)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2011-12-20 Created: 2011-12-20 Last updated: 2017-12-08Bibliographically approved
2. Synthesis of thienoimidazo[4,5-b]pyridines and thenylidenoimidazolinones
Open this publication in new window or tab >>Synthesis of thienoimidazo[4,5-b]pyridines and thenylidenoimidazolinones
2005 (English)In: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 65, no 10, 2369-2380 p.Article in journal (Refereed) Published
Abstract [en]

The two isomers 2-amino-1-methylimidazo[4,5-b]thieno[3,2-e]pyridine (3) and 2-amino-1-methylimidazo[4,5-b]thieno[2,3-e]pyridine (4) were synthesized by the Friedlander reaction starting from creatinine and the appropriate aminothiophenecarbaldehydes (11 and 13). Creatinine was also condensed with 2-nitro-3-thiophenecarbaldehyde (10) in ethylene glycol to yield the 2-amino-1-methyl-5-[2-(2-nitro-3-thenylidene)]-2-imidazolin-4-one (7a), with 3-amino-2-thiophenecarbaldehyde (13) under Perkin conditions to yield 2-acetamido-5-[2-(3-acetamido-2-thenylidene)]-1-methyl-2-imidazolin-4-on e (8), and with 4-azido-3-thiophenecarbaldehyde (17) in acetic acid to yield 2-amino-5[2-(4-azido-3-thenylidene)]-1-methyl-2-imidazolin-4-one (9). The thenylidenoimidazolinonc (8) was converted into compound (4).

National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-14440 (URN)10.3987/COM-05-10486 (DOI)000232582400006 ()
Available from: 2012-01-31 Created: 2011-12-23 Last updated: 2017-12-08Bibliographically approved
3. Synthesis of imidazo[4,5-e]-2,1,3-benzoselenadiazoles and derivatives thereof
Open this publication in new window or tab >>Synthesis of imidazo[4,5-e]-2,1,3-benzoselenadiazoles and derivatives thereof
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-31998 (URN)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2017-02-08 Created: 2017-02-08 Last updated: 2017-02-08Bibliographically approved
4. Classical conditions of Suzuki, Stille, Heck and Sonogashira couplings applied on 4- and 5-substituted 2,1,3-benzoselenadiazoles
Open this publication in new window or tab >>Classical conditions of Suzuki, Stille, Heck and Sonogashira couplings applied on 4- and 5-substituted 2,1,3-benzoselenadiazoles
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-31999 (URN)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2017-02-08 Created: 2017-02-08 Last updated: 2017-02-08Bibliographically approved

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