Science of Synthesis

Hapiot, F.; Monflier, E., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 778.

The furanone ring moiety occurs as a subunit in many natural products. This core unit is the key structure to induce a wide range of biological activities such as antimicrobial, antifungal, anti-inflammatory, anticancer, and antiviral. 3,4,5-Trisubstituted furan-2(5H)-one derivatives (e.g., ‌6‌) are synthesized by reaction of an aniline, diethyl acetylenedicarboxylate, and a benzaldehyde using β-cyclodextrin as a promoter (‌Scheme 6‌).[‌24‌] The existence of an inclusion complex between aniline and β-cyclodextrin has been evidenced and supports the idea that the hydrophobic environment of β-cyclodextrin facilitates the formation of lactones via an inclusion complex of the aniline–diethyl acetylenedicarboxylate carbanion which is further trapped by the aldehyde to generate the desired butenolide synthon. The primary and secondary hydroxy groups of β-cyclodextrin are believed to stabilize the inclusion complex. β-Cyclodextrin is recovered and reused. After the reaction, the β-cyclodextrin is recovered and further used with the same substrates as a mass-transfer additive. The yields of 3,4,5-trisubstituted furan-2(5H)-one after two to three recycles are almost the same.

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References