1,2,3,6-Tetrahydropyridine-4-carboxylic acid (isoguvacine) and related 2-and/or 6-methylated analogues (1-4) were synthesized using the methoxycarbonylation [Pd(OAc)(2), PPh(3), CO, MeOH)] of their corresponding vinylic triflates. Analogue (5), the 6-methyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid was obtained after a reductive deoxygenation of the corresponding beta-keto ester.
Rohr, M., Chayer, S., Garrido, F., Mann, A., Taddei, M., Wermuth, C.G. (1996). Synthesis of 2- or/and 6-methylated analogues of isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) a GABA(A) agonist. HETEROCYCLES, 43(10), 2131-2138 [10.3987/com-96-7522].
Synthesis of 2- or/and 6-methylated analogues of isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) a GABA(A) agonist
Taddei, Maurizio;
1996-01-01
Abstract
1,2,3,6-Tetrahydropyridine-4-carboxylic acid (isoguvacine) and related 2-and/or 6-methylated analogues (1-4) were synthesized using the methoxycarbonylation [Pd(OAc)(2), PPh(3), CO, MeOH)] of their corresponding vinylic triflates. Analogue (5), the 6-methyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid was obtained after a reductive deoxygenation of the corresponding beta-keto ester.
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https://hdl.handle.net/11365/31390
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