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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.

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.

SUBMITTER: Yaragorla S

PROVIDER: S-EPMC6044873 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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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.

Yaragorla Srinivasarao S Dada Ravikrishna R Rajesh P P Sharma Manju M

ACS omega 20180309 3

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 experi ...[more]

PMID: 30023853

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