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Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C(sp3)–H Functionalization, and Azacyclization
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Abstract
A one-pot, sequential Meyer–Schuster (MS) rearrangement of oxindole-derived propargyl alcohols to the corresponding α,β-unsaturated enones and their anti-Michael addition, followed by intramolecular azacyclization is described in a highly regioselective manner using Ca(OTf)2 as the promoter. Further, we described the one-pot MS rearrangement, followed by C(sp3)–H functionalization of 2-methyl azaarenes at α-carbon of these doubly activated alkenes. Control experiments and computational calculations were performed to propose the reaction mechanism.
American Chemical Society (ACS)
Title: Highly Regioselective Synthesis of Oxindolyl-Pyrroles
and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement,
Anti-Michael Addition/C(sp3)–H Functionalization,
and Azacyclization
Description:
Abstract
A one-pot, sequential Meyer–Schuster (MS) rearrangement of oxindole-derived propargyl alcohols to the corresponding α,β-unsaturated enones and their anti-Michael addition, followed by intramolecular azacyclization is described in a highly regioselective manner using Ca(OTf)2 as the promoter.
Further, we described the one-pot MS rearrangement, followed by C(sp3)–H functionalization of 2-methyl azaarenes at α-carbon of these doubly activated alkenes.
Control experiments and computational calculations were performed to propose the reaction mechanism.
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