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

[Image: see text] 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 t...

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Autores principales: Yaragorla, Srinivasarao, Dada, Ravikrishna, Rajesh, P., Sharma, Manju
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044873/
https://www.ncbi.nlm.nih.gov/pubmed/30023853
http://dx.doi.org/10.1021/acsomega.8b00147
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author Yaragorla, Srinivasarao
Dada, Ravikrishna
Rajesh, P.
Sharma, Manju
author_facet Yaragorla, Srinivasarao
Dada, Ravikrishna
Rajesh, P.
Sharma, Manju
author_sort Yaragorla, Srinivasarao
collection PubMed
description [Image: see text] 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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spelling pubmed-60448732018-07-16 Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization Yaragorla, Srinivasarao Dada, Ravikrishna Rajesh, P. Sharma, Manju ACS Omega [Image: see text] 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. American Chemical Society 2018-03-09 /pmc/articles/PMC6044873/ /pubmed/30023853 http://dx.doi.org/10.1021/acsomega.8b00147 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Yaragorla, Srinivasarao
Dada, Ravikrishna
Rajesh, P.
Sharma, Manju
Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization
title Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization
title_full Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization
title_fullStr Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization
title_full_unstemmed Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization
title_short Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer–Schuster Rearrangement, Anti-Michael Addition/C((sp(3)))–H Functionalization, and Azacyclization
title_sort highly regioselective synthesis of oxindolyl-pyrroles and quinolines via a one-pot, sequential meyer–schuster rearrangement, anti-michael addition/c((sp(3)))–h functionalization, and azacyclization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044873/
https://www.ncbi.nlm.nih.gov/pubmed/30023853
http://dx.doi.org/10.1021/acsomega.8b00147
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