[1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes

A new simple one-pot two-step protocol for the synthesis of 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate from 2-(2-(benzylamino)benzylidene)malonate under the action of BF3·Et2O was developed. It was shown that the reaction proceeds through the formation of a stable iminium intermediate containin...

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Autores principales: Zaitseva, Elvira R., Ivanov, Dmitrii S., Smirnov, Alexander Yu., Mikhaylov, Andrey A., Baleeva, Nadezhda S., Baranov, Mikhail S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414529/
https://www.ncbi.nlm.nih.gov/pubmed/36014513
http://dx.doi.org/10.3390/molecules27165270
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author Zaitseva, Elvira R.
Ivanov, Dmitrii S.
Smirnov, Alexander Yu.
Mikhaylov, Andrey A.
Baleeva, Nadezhda S.
Baranov, Mikhail S.
author_facet Zaitseva, Elvira R.
Ivanov, Dmitrii S.
Smirnov, Alexander Yu.
Mikhaylov, Andrey A.
Baleeva, Nadezhda S.
Baranov, Mikhail S.
author_sort Zaitseva, Elvira R.
collection PubMed
description A new simple one-pot two-step protocol for the synthesis of 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate from 2-(2-(benzylamino)benzylidene)malonate under the action of BF3·Et2O was developed. It was shown that the reaction proceeds through the formation of a stable iminium intermediate containing a difluoroboryl bridge in the dicarbonyl fragment of the molecule.
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spelling pubmed-94145292022-08-27 [1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes Zaitseva, Elvira R. Ivanov, Dmitrii S. Smirnov, Alexander Yu. Mikhaylov, Andrey A. Baleeva, Nadezhda S. Baranov, Mikhail S. Molecules Article A new simple one-pot two-step protocol for the synthesis of 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate from 2-(2-(benzylamino)benzylidene)malonate under the action of BF3·Et2O was developed. It was shown that the reaction proceeds through the formation of a stable iminium intermediate containing a difluoroboryl bridge in the dicarbonyl fragment of the molecule. MDPI 2022-08-18 /pmc/articles/PMC9414529/ /pubmed/36014513 http://dx.doi.org/10.3390/molecules27165270 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zaitseva, Elvira R.
Ivanov, Dmitrii S.
Smirnov, Alexander Yu.
Mikhaylov, Andrey A.
Baleeva, Nadezhda S.
Baranov, Mikhail S.
[1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes
title [1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes
title_full [1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes
title_fullStr [1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes
title_full_unstemmed [1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes
title_short [1,5]-Hydride Shift Triggered N-Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes
title_sort [1,5]-hydride shift triggered n-dealkylative cyclization into 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via boronate complexes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414529/
https://www.ncbi.nlm.nih.gov/pubmed/36014513
http://dx.doi.org/10.3390/molecules27165270
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