Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 1, Pages 266-275Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201841y
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Funding
- Spanish MICINN [CTQ2010-16959, CSD2007-00006]
- Basque Government (GV-EJ) [IT-324-07]
- MICINN
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In this paper, a fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and alpha-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogues can be obtained from commercial sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.
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