Article ID Journal Published Year Pages File Type
5225651 Tetrahedron 2006 7 Pages PDF
Abstract

The aza-Diels-Alder reactions of two 2-aminophenols in combination with six substituted benzaldehydes and two electron-rich cyclic alkenes were investigated under controlled microwave heating. The reactions were carried out in the presence of a catalytic amount of CF3CO2H in MeCN at 60 °C for 15 min, affording highly functionalized 8-hydroxy-1,2,3,4-tetrahydroquinolines in 39-59% isolated yields and in 36:64-16:84 diastereomer ratios in favor of the trans isomers. The microwave-heated three-component aza-Diels-Alder reactions completed in significantly reduced reaction time to give the same level of chemical yield and diastereomer ratio obtained from the room temperature reaction.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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