Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Interrupting Base-Mediated Benzofuran Ring Transformation with Michael Acceptors

Interrupting Base-Mediated Benzofuran Ring Transformation with Michael Acceptors
Rashmi Sharma, Chepuri V. Ramana, Kolluru Srinivas
A simple two-stage approach for the synthesis of 3-(2-arylbenzofuran-3-yl)propanoates and propanamides has been developed employing simple acrylates and acrylamides and readily available 3-aroylbenzofurans. The key step of this process involves a base-mediated ring opening of the 3-aroylbenzofurans and subsequent Michael addition of the resulting 1,3-dicarbonyl intermediate with acrylate/acrylamide, followed by the deformylation in one-pot. The resulting products undergo an acid-mediated dehydrative cyclization to arrive at these targets.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01267

DOI: 10.1021/acs.joc.7b01267

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