A one-pot ring-closure and ring-opening sequence for the cascade synthesis of dihydrofurofurans and functionalized furans?

Organic & Biomolecular Chemistry Pub Date: 2021-08-07 DOI: 10.1039/D1OB01300A

Abstract

We have developed a simple novel ring-closure and ring-opening pathway using an organo-base system for the synthesis of highly substituted dihydrofurofuran and furan frameworks via a triethylamine-catalyzed one-pot three-component reaction. The protocol involved a Knoevenagel and Michael adduct via Paal–Knorr cyclization with aromatic/aliphatic glyoxal and 2-cyanoacetophenone under mild and heating conditions with excellent yields through a simple filtration method. The merits of this methodology, including the use of easily available feedstocks and an inexpensive catalyst, Gram-scale synthesis, wide functional group tolerance, an open-air reaction setup, and no need for workup and column-chromatography procedures, make the developed methodology a practical way to access dihydrofurofurans and functionalized furans.

Graphical abstract: A one-pot ring-closure and ring-opening sequence for the cascade synthesis of dihydrofurofurans and functionalized furans
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