Environmentally benign syntheses of flavanones

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• 作者：Po-Yuan Chen^a ; Tzu-Pin Wang^a ; Michael Y. Chiang^b ; Keng-Shian Huang^c ; Cherng-Chyi Tzeng^a ; Yi-Long Chen^a ; Eng-Chi Wang^a ; ^{enchwa@kmu.edu.tw"" rel=""nofollow}
• 关键词：Flavanones ; Claisen– ; Schmidt reaction ; Mitsunobu’ ; s reaction ; Intramolecular cyclization
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：10 June 2011
• 年：2011
• 卷：67
• 期：23
• 页码：4155-4160
• 全文大小：355 K

文摘

Mild and environmentally benign methods for the syntheses of flavanones are described. The reaction of o-hydroxyacetophenones (1) and benzaldehydes (2) in water in the presence of DABCO at room temperature gave 3-hydroxy-1-(2-hydroxylphenyl)-3-arylpropan-1-ones (3a–i) as intermediates. Followed by an intramolecular dehydration of the 3a–i with the modified Mitsunobu’s reaction, the target flavanones (4a–i) were obtained. Moreover, the reaction of 1 and 2 at the same conditions but at reflux gave flavanones in one pot with good yields.