Synthesis p. 479 - 480 (1988)
Update date:2022-08-05
Topics:
Mittelbach, Martin
A new and easy synthesis of 6-methyl-4(1H)-pyridone-3-carboxylic acid (5), an important component of broad spectrum cephalosporins, is described.It starts from the readily available ethyl 4-hydroxy-6-methyl-2(1H)-pyridone-3-carboxylate (1), which is treated with phosphoryl chloride to give ethyl 2,4-dichloro-6-methylpyridine-3-carboxylate (2).Selective substitution of the chlorine in 4-position with alkoxide ion leads to the 4-alkoxypyridine derivatives 3.Hydrogenolysis of 3 affords ethyl 4-alkoxy-6-methyl-pyridine-3-carboxylates 4; which are hydrolysed to 5 in one step.
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Doi:10.1021/ol802970g
(2009)Doi:10.1021/ja00146a018
(1995)Doi:10.1021/jm00398a018
(1988)Doi:10.1016/S0040-4039(00)95996-3
(1987)Doi:10.1016/S0040-4039(00)00378-6
(2000)Doi:10.1039/jr9600003457
(1960)
