Practical synthesis of a functionalized 1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid |
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Authors: | Samir A.P. QuintilianoLuiz F. Silva Jr. |
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Affiliation: | Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo, SP, Brazil |
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Abstract: | The synthesis of a functionalized 1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid has been performed in 10 steps from the readily available dimedone. Only three purifications by flash chromatography are required through the whole sequence. The key step is the reaction between a dimedone derivative and a chlorotetrolic ester, that gives a tetrasubstituted benzene ring (through a Diels-Alder/retro- Diels-Alder process) bearing the substituents in the suitable positions for further functionalization. |
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Keywords: | 1-Oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Diels-Alder Tetrasubstituted benzene |
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