期刊论文详细信息
Journal of the Brazilian Chemical Society
A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
Lemos, Telma L. G. de1  Lopes, Regina C. V.1  Universidade Federal do Ceará, Fortaleza, Brazil1  Oliveira, Maria da Conceição F. de1  Mattos, Marcos C. de1 
关键词: Phase Transfer Catalysis;    annulation;    Michael reaction;   
DOI  :  10.1590/S0103-50532005000600023
学科分类:化学(综合)
来源: SciELO
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【 摘 要 】

The Michael addition of ethyl acetoacetate 1 to chalcone 2 under Solid/Liquid Phase Transfer Catalysis (SL-PTC), solvent free, afforded Michael adduct 3 and an annulated compound 4 in good yield. The cyclic compound 4 was obtained in the majority via an annulation process of the Michael adduct 3. The proportion of 4 in the ratio of 3/4 was dependant on the structure of the quaternary ammonium cation. The results were interpreted on the basis of the organophilicity and accessibility of the catalysts as well as by invoking a 6-membered ring transition state for the formation of 4 due to the chelation level with Q+.

【 授权许可】

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