Practical synthesis of a functionalized 1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
06/11/2013
06/11/2013
2012
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| Resumo |
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. (C) 2012 Elsevier Ltd. All rights reserved. CNPq FAPESP CAPES |
| Identificador |
TETRAHEDRON LETTERS, OXFORD, v. 53, n. 29, pp. 3808-3810, 2012 0040-4039 http://www.producao.usp.br/handle/BDPI/42673 10.1016/j.tetlet.2012.05.060 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD OXFORD |
| Relação |
TETRAHEDRON LETTERS |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #1-OXO-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID #1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID #DIELS-ALDER #TETRASUBSTITUTED BENZENE #ABSOLUTE-CONFIGURATION #BIOLOGICAL EVALUATION #EFFICIENT SYNTHESIS #IN-VITRO #INHIBITORS #DERIVATIVES #DESIGN #DIENOPHILES #ESTERS #CHEMISTRY, ORGANIC |
| Tipo |
article original article publishedVersion |
