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Solid-phase synthesis of thiazolo[4,5-b]pyridine derivatives using Friedländer reaction. 2010

Taeho Lee, and Doohyun Lee, and Ill Young Lee, and Young-Dae Gong
Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology, Yuseong-gu, Daejeon, Korea. taeholee@krict.re.kr

Traceless solid-phase synthesis of 2,5,6,7-tetrasubstituted thiazolo[4,5-b]pyridine derivatives is described. Thorpe-Ziegler type cyclization of solid supported cyanocarbonimidodithioate with alpha-halo ketones afforded thiazole resin, which were converted to the desired thiazolopyridine resin by the Friedländer protocol under microwave irradiation conditions. After oxidation of sulfides to sulfones, nucleophilic desulfonative substitution with amines gave the target thiazolo[4,5-b]pyridine derivatives in good overall yields.

UI MeSH Term Description Entries
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D020650 Combinatorial Chemistry Techniques A technology, in which sets of reactions for solution or solid-phase synthesis, is used to create molecular libraries for analysis of compounds on a large scale. Chemistry Techniques, Combinatorial,Techniques, Combinatorial Chemistry,Chemistry Technic, Combinatorial,Chemistry Technics, Combinatorial,Chemistry Technique, Combinatorial,Combinatorial Chemistry Technic,Combinatorial Chemistry Technics,Combinatorial Chemistry Technique,Technic, Combinatorial Chemistry,Technics, Combinatorial Chemistry,Technique, Combinatorial Chemistry

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