Synthesis of tetrahydropyrido[2,3-b]pyrazine scaffolds from 2,3,5,6-tetrafluoropyridine derivatives |
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Authors: | Christopher A. Hargreaves Rachel Slater Judith A.K. Howard |
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Affiliation: | a Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK b Chemical Crystallography Group, Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK c GlaxoSmithKline Pharmaceuticals plc, New Frontiers Science Park North, Fourth Avenue, Harlow, Essex CM19 5AW, UK |
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Abstract: | Reactions between N,N′-dimethylethylene diamine and a range of 2,3,5,6-tetrafluoropyridine derivatives provided ready access to the corresponding tetrahydropyrido[2,3-b]pyrazine systems if the substituent located at the 4-position of the pyridine ring was either hydrogen or an electron withdrawing substituent. In contrast, the presence of electron donating substituents at the 4-position made the formation of ring-fused products much more difficult. The two-step sequential nucleophilic substitution procedures from pentafluoropyridine gave convenient and adaptable methodology for the synthesis of polyfunctional tetrahydropyrido[2,3-b]pyrazine scaffolds of interest to the life science discovery arenas. |
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