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Published on: February 7, 2019
Acid-Regulated Selective Synthesis of Benzofuran Derivatives via Single-Component BDA Retro-Aldol/Michael Addition
Shuhong Wang1,2, Xinran Niu2, Haojia Zhou2
1Pingyuan Laboratory, Key Laboratory of Antiviral Drugs, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Abstract:
The acid-controlled single-component retro-aldol/Michael addition cascade reaction and [4 + 2] cycloaddition of benzofuran-derived azadienes (BDAs) are reported for the first time. Under the conditions of trifluoromethanesulfonic acid as the catalyst and with the addition of water, BDAs initiate the retro-aldol reaction, followed by a 1,4-Michael addition, yielding (arylmethylene)bis(dibenzofuran) products with excellent yields and broad substrate applicability. This represents the first application of BDAs in a retro-aldol reaction. In contrast, in the absence of water and with boron trifluoride etherate as the catalyst, BDAs undergo a [4 + 2] cycloaddition reaction, constructing the spiro[benzofuran-2,3'-benzofuro[3,2-b]pyridine] framework with high yields and diastereoselectivity. The method features mild conditions and high atom economy, and provides a new approach for constructing benzofuran scaffold derivatives.
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