Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines

Herein, we report a simple and metal-free protocol for the synthesis of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines. The present method under mild reaction conditions with wide functional group compatibility gives several unexplored N-substituted/unsubstituted 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]qu...

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Autores principales: Ramu, Gopathi, Ambala, Srinivas, Nanubolu, Jagadeesh Babu, Nagendra Babu, Bathini
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9074153/
https://www.ncbi.nlm.nih.gov/pubmed/35530667
http://dx.doi.org/10.1039/c9ra07831b
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author Ramu, Gopathi
Ambala, Srinivas
Nanubolu, Jagadeesh Babu
Nagendra Babu, Bathini
author_facet Ramu, Gopathi
Ambala, Srinivas
Nanubolu, Jagadeesh Babu
Nagendra Babu, Bathini
author_sort Ramu, Gopathi
collection PubMed
description Herein, we report a simple and metal-free protocol for the synthesis of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines. The present method under mild reaction conditions with wide functional group compatibility gives several unexplored N-substituted/unsubstituted 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines and marinoquinolines in good to excellent yields. Mechanistic insights for the synthesis of N-substituted pyrroloquinolines reveal the ring expansion of 3-ylideneoxindoles and H-shift as the key steps.
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spelling pubmed-90741532022-05-06 Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines Ramu, Gopathi Ambala, Srinivas Nanubolu, Jagadeesh Babu Nagendra Babu, Bathini RSC Adv Chemistry Herein, we report a simple and metal-free protocol for the synthesis of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines. The present method under mild reaction conditions with wide functional group compatibility gives several unexplored N-substituted/unsubstituted 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolines and marinoquinolines in good to excellent yields. Mechanistic insights for the synthesis of N-substituted pyrroloquinolines reveal the ring expansion of 3-ylideneoxindoles and H-shift as the key steps. The Royal Society of Chemistry 2019-10-30 /pmc/articles/PMC9074153/ /pubmed/35530667 http://dx.doi.org/10.1039/c9ra07831b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Ramu, Gopathi
Ambala, Srinivas
Nanubolu, Jagadeesh Babu
Nagendra Babu, Bathini
Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
title Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
title_full Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
title_fullStr Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
title_full_unstemmed Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
title_short Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
title_sort regioselective ring expansion followed by h-shift of 3-ylidene oxindoles: a convenient synthesis of n-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9074153/
https://www.ncbi.nlm.nih.gov/pubmed/35530667
http://dx.doi.org/10.1039/c9ra07831b
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