J. Org. Chem. 2026, 91 (26), 8849-8855
DOI: 10.1021/acs.joc.6c00516
Buravov O. V.; Shishkina S. V.; Chebanov V. A.
We report an aqueous phosphoric acid-promoted [3,3]-sigmatropic rearrangement of 2-(furan-3-yl)-2-(arylamino)acetonitriles for the regioselective synthesis of polysubstituted 2-arylfurans. This transition-metal-free method proceeds under mild, room-temperature conditions with broad functional-group tolerance. The utility of these products is showcased through their efficient one-step transformation into previously undescribed 5,6-dihydro-4H-benzo[b]furo[2,3-d]azepine derivatives. This approach aligns with green chemistry principles and expands the synthetic utility of heteroaromatic rearrangements.