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 | Zendy

Srinivasarao Yaragorla | Zendy; Ravikrishna Dada | Zendy; P. Rajesh | Zendy; Manju Sharma | Zendy

Open Access

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

Author(s) -

Srinivasarao Yaragorla,

Ravikrishna Dada,

P. Rajesh,

Manju Sharma

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b00147

Subject(s) - regioselectivity , surface modification , michael reaction , combinatorial chemistry , chemistry , organic chemistry , catalysis

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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