Synthesis

Selective reduction of the endocyclic double bond of 3-substituted coumarins by Hantzsch 1, 4-dihydropyridine

Z Liu, Q Liu, W Zhang, R Mu, L Yang, ZL Liu, W Yu

Index: Liu, Zhengang; Liu, Qiang; Zhang, Wei; Mu, Ruizhu; Yang, Li; Liu, Zhong-Li; Yu, Wei Synthesis, 2006 , # 5 p. 771 - 774

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Citation Number: 15

Abstract

In the case of coumarin 1h, however, when anhydrous EtOH was used as solvent, the transesterified product 2h′, instead of the expected 3,4-dihydrocoumarin 2h, was obtained in 90% yield (Table [1] , entry 8). Apparently, the cyano group renders 2h labile towards the nucleophilic EtOH. This problem was solved by using anhydrous CH 3 CN or anhydrous THF as the solvent, and 2h was obtained in high yield. The best result was achieved when the reaction was carried out in ...