Chemical cascades in water for the synthesis of functionalized aromatics from furfurals
Chemical cascades in water for the synthesis of functionalized aromatics from furfurals
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DOI：
10.1039/c5gc02935j
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发表时间：
2016-01-01
期刊：
影响因子：
9.8
通讯作者：
Hailes, Helen C.
中科院分区：
文献类型：
--
作者：
Higson, Sally;Subrizi, Fabiana;Hailes, Helen C.
已经开发出在水中从糠醛到多取代芳香族化合物的一锅合成路线，无需任何有机溶剂。该反应通过无催化的一锅反应级联进行，形成腙衍生物，与亲二烯体原位环加成，然后芳构化。通过完全控制取代模式，可以获得一系列取代的邻苯二甲酰亚胺。该反应还扩展到其他亲二烯体和二烯2-呋喃基丙烯醛。邻苯二甲酰亚胺产品经过进一步精制，可生产多种多取代苯，包括药学相关化合物。
One-pot synthetic routes from furfurals to polysubstituted aromatic compounds have been developed in water, without the need for any organic solvents. The reaction proceeds via an uncatalysed, one-pot reaction cascade through formation of a hydrazone derivative, in situ cycloaddition with a dienophile, then aromatisation. A range of substituted phthalimides can be accessed with complete control over the substitution pattern. The reaction was also extended to other dienophiles and the diene 2-furylacrolein. The phthalimide products were further elaborated to produce a variety of polysubstituted benzenes including pharmaceutically relevant compounds.