One-pot combinatorial synthesis of 4-aryl-1H-thiopyrano[3,4-b]pyridine-5-one derivatives.
A simple and efficient method for the combinatorial synthesis of highly substituted thiopyrano[3,4-b]pyridin-5(4H)-one, thiopyrano[3,4-b]quinoline-4,6(3H,5H)-dione, dithiopyrano[3,4-b:4',3'-e]pyridine-4,6(1H,3H)-dione, and pyrazolo[3,4-b]thiopyrano[4,3-e]pyridin-5(1H)-one derivatives has been developed. The synthesis was achieved via one-pot multicomponent reaction of aromatic aldehyde, 2H-thiopyran-3,5(4H,6H)-dione and enamine (such as the derivatives of amine and 1,3-dicarbonyl compounds and 3-methyl-1-phenyl-1H-pyrazol-5-amine) in glacial acetic acid. This procedure features short reaction time, generally good to excellent yields, easily available starting materials, and operational simplicity. This chemistry provides an efficient and promising synthetic strategy to diversity-oriented construction of the thiopyrano[3,4-b]pyridine skeleton.
Yao
Chang-Sheng
CS
School of Chemistry and Chemical Engineering, Xuzhou Normal University, and Key Laboratory of Biotechnology for Medicinal Plant, Xuzhou, Jiangsu, 221116, P.R. China.
Wang
Cui-Hua
CH
Jiang
Bei
B
Tu
Shu-Jiang
SJ
D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries
D011714:Pyrans; D011725:Pyridines; D011728:Pyridones; D054852:Small Molecule Libraries