Issue 34, 2021

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

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

Supplementary files

Article information

Article type
Paper
Submitted
05 Jul 2021
Accepted
30 Jul 2021
First published
07 Aug 2021

Org. Biomol. Chem., 2021,19, 7409-7419

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

M. B. Yadav and Y. T. Jeong, Org. Biomol. Chem., 2021, 19, 7409 DOI: 10.1039/D1OB01300A

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