Preparation of 2-amino-4H-chromene derivatives from coumarins in basic media
Preparation of 2-amino-4H-chromene derivatives from coumarins in basic media
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DOI：
10.1002/ejoc.200500495
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发表时间：
2006-01-30
影响因子：
2.8
通讯作者：
Cravotto, G
中科院分区：
文献类型：
--
作者：
Curini, M;Rosati, O;Cravotto, G
香豆素与氰基乙酸酯在亲核碱(烷氧基或哌啶)存在下的反应遵循一条有趣的途径，包括香豆素骨架重排和通过香豆酸衍生物的Michael加成，得到取代的4H-色烯骨架。这一过程的特殊行为会影响所能获得的化合物的性能和类型。我们证明了过量氰基乙酸酯的使用提供了高产率的4H-色烯衍生物。对这一过程所涉及的机理进行了解释。(C)Wiley-VCH Verlag GmbH&Co.KGaA，69451，德国温海姆)。
The reaction of coumarin with cyanoacetate derivatives in the presence of a nucleophilic base (alkoxides or piperidine) follows an interesting pathway that involves both a coumarin skeletal rearrangement and a Michael addition, via a coumaric acid derivative, to afford a substituted 4H-chromene skeleton. The particular behavior of this process influences the performance and the type of compounds that can be obtained. We demonstrate that the use of an excess of cyanoacetate affords the 4H-chromene derivative in high yield. An explanation of the mechanism involved in this process is proposed. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).