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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 (sp 3 ) -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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Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C<sub>(sp<sup>3</sup>)</sub>–H Functionalization, and Azacyclization

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

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