Synthetic Applications of Nitropyridine Derivatives
Doctoral thesis
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http://hdl.handle.net/11250/247604Utgivelsesdato
2010Metadata
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- Institutt for kjemi [1404]
Sammendrag
The present work represents a continuation of the investigation of the chemistry of nitropyridine derivatives, based on the methodology for nitration of pyridines developed by Professor Jan M. Bakke and co-workers at NTNU. Nitropyridines have been utilized as substrates for the formation of novel bis- and tris-heterocyclic compounds, and new synthetic routes to fused heterocycles have been developed.
Several new β-carboline analogues and fused azacinnolines have been prepared based on a Suzuki coupling and subsequent cyclization approuch. The formation of 4-isocyanobut-2-enenitrile and 3-cyanopyrrole products by ring opening and ring contraction of 3-pyridyl nitrenes, respectively, is reported. 7-Azacinnolin-4(1H)-one has been prepared and tautomery investigated by NMR. The general ability of appropriate pyridyl compunds to undergo Friedländer condensation to give different 1,7-naphthyridines has been demonstrated. Bis-heterocyclic products have been prepared from methyl/allylpyridylketones fromed by Weinreb tranformations, and a method has been developed to allow for the preperation of reactive pure pyridylvinylketones to be used in further reactions, such as Diels-Alder cycloaddition reactions.
Består av
Stockmann, Vegar; Eriksen, Kristine L.; Fiksdahl, Anne. Preparation of novel pyridine-fused tris-heterocycles; pyrido[4,3-e]pyrrolo-/pyrido[4,3-e]furano[2,3-c]pyridazines and pyrido[3,4-b]pyrrolo[3,2-d]pyrrole. Tetrahedron. (ISSN 0040-4020). 64(49): 11180-11184, 2008. 10.1016/j.tet.2008.09.051.Stockmann, Vegar; Bakke, Jan M.; Bruheim, Per; Fiksdahl, Anne. Formation of new 4-isocyanobut-2-enenitriles by thermal ring cleavage of 3-pyridyl azides. Tetrahedron. (ISSN 0040-4020). 65(18): 3668-3672, 2009. 10.1016/j.tet.2009.02.072.
Hansen, Lars Kr.; Stockmann, Vegar; Fiksdahl, Anne. 8H-6-Azathieno[2,3-b]indole. Acta Crystallographica Section E - Structure Reports Online. (ISSN 1600-5368): CCDC 778181, 2010.
Hansen, Lars Kr.; Stockmann, Vegar; Fiksdahl, Anne. 7-azathieno[3,2-c]cinnoline. Acta Crystallographica Section E - Structure Reports Online. (ISSN 1600-5368). 63: O3290-U4201, 2007. 10.1107/S1600536807029947.
Hansen, Lars Kr.; Stockmann, Vegar; Fiksdahl, Anne. 7-Azathieno[2,3-c] cinnoline. Acta Crystallographica Section E - Structure Reports Online. (ISSN 1600-5368). 63: O3896-U3816, 2007. 10.1107/S1600536807041335.
Stockmann, Vegar; Kaspersen, Svein Jacob; Nicolaisen, Alexander; Fiksdahl, Anne. Studies on reactive pyridylketones formed by Weinreb transformations. .