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

Srinivasarao Yaragorla, Ravikrishna Dada, P. Rajesh, Manju Sharma

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21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2934-2946
Number of pages13
JournalACS Omega
Volume3
Issue number3
DOIs
StatePublished - Mar 31 2018
Externally publishedYes

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© 2018 American Chemical Society.

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