Approach to the library of fused pyridine-4-carboxylic acids by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles.
A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.
Volochnyuk
Dmitriy M
DM
Department of Chemistry, Kyiv National Taras Shevchenko University, Kyiv 01033, Ukraine. d.volochnyuk@enamine.net
Ryabukhin
Sergey V
SV
Plaskon
Andrey S
AS
Dmytriv
Yuri V
YV
Grygorenko
Oleksandr O
OO
Mykhailiuk
Pavel K
PK
Krotko
Dmitriy G
DG
Pushechnikov
Alexei
A
Tolmachev
Andrey A
AA
D020650:Combinatorial Chemistry Techniques; D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006868:Hydrolysis; D007539:Isonicotinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011773:Pyruvates / Q000737:chemistry*; D054852:Small Molecule Libraries; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007539:Isonicotinic Acids; D011773:Pyruvates; D054852:Small Molecule Libraries