Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9: Chemistry of aminophenols |
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| Authors: | Xinglong Xing Wei-Min Dai |
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| Affiliation: | a Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, China
b Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China |
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| 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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| Keywords: | Microwave Aza-Diels-Alder cycloaddition 2-Aminophenols Tetrahydroquinolines |
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