Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement

[Image: see text] The synthesis of bromo-substituted indeno[1,2-b]pyridin-2-ones and 3-iodo-5-benzyl-substituted 2-pyridones, starting from easily available 6-benzyl-3,6-dihydropyridin-2(1H)-ones, triggered by NBS and NIS, respectively, is described. In both syntheses, a transfer of a benzyl group f...

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Autores principales: Sośnicki, Jacek G., Borzyszkowska-Ledwig, Aleksandra, Idzik, Tomasz J., Lubowicz, Magdalena M., Maciejewska, Gabriela, Struk, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9706813/
https://www.ncbi.nlm.nih.gov/pubmed/36367325
http://dx.doi.org/10.1021/acs.orglett.2c03361
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author Sośnicki, Jacek G.
Borzyszkowska-Ledwig, Aleksandra
Idzik, Tomasz J.
Lubowicz, Magdalena M.
Maciejewska, Gabriela
Struk, Łukasz
author_facet Sośnicki, Jacek G.
Borzyszkowska-Ledwig, Aleksandra
Idzik, Tomasz J.
Lubowicz, Magdalena M.
Maciejewska, Gabriela
Struk, Łukasz
author_sort Sośnicki, Jacek G.
collection PubMed
description [Image: see text] The synthesis of bromo-substituted indeno[1,2-b]pyridin-2-ones and 3-iodo-5-benzyl-substituted 2-pyridones, starting from easily available 6-benzyl-3,6-dihydropyridin-2(1H)-ones, triggered by NBS and NIS, respectively, is described. In both syntheses, a transfer of a benzyl group from the C6 to C5 lactam position occurred, indicating a novel aza-semipinacol-type rearrangement. Identification of intermediate compounds in both transformations supported the proposed reaction mechanisms. In the process of checking the scope of the method’s application, functionalized indeno[1,2-b]pyridin-2-ones and 5-benzyl-2-pyridones were obtained.
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spelling pubmed-97068132022-11-30 Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement Sośnicki, Jacek G. Borzyszkowska-Ledwig, Aleksandra Idzik, Tomasz J. Lubowicz, Magdalena M. Maciejewska, Gabriela Struk, Łukasz Org Lett [Image: see text] The synthesis of bromo-substituted indeno[1,2-b]pyridin-2-ones and 3-iodo-5-benzyl-substituted 2-pyridones, starting from easily available 6-benzyl-3,6-dihydropyridin-2(1H)-ones, triggered by NBS and NIS, respectively, is described. In both syntheses, a transfer of a benzyl group from the C6 to C5 lactam position occurred, indicating a novel aza-semipinacol-type rearrangement. Identification of intermediate compounds in both transformations supported the proposed reaction mechanisms. In the process of checking the scope of the method’s application, functionalized indeno[1,2-b]pyridin-2-ones and 5-benzyl-2-pyridones were obtained. American Chemical Society 2022-11-11 2022-11-25 /pmc/articles/PMC9706813/ /pubmed/36367325 http://dx.doi.org/10.1021/acs.orglett.2c03361 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Sośnicki, Jacek G.
Borzyszkowska-Ledwig, Aleksandra
Idzik, Tomasz J.
Lubowicz, Magdalena M.
Maciejewska, Gabriela
Struk, Łukasz
Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement
title Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement
title_full Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement
title_fullStr Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement
title_full_unstemmed Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement
title_short Divergent Synthesis of Functionalized Indenopyridin-2-ones and 2-Pyridones via Benzyl Group Transfer: Two Cases of Aza-semipinacol-Type Rearrangement
title_sort divergent synthesis of functionalized indenopyridin-2-ones and 2-pyridones via benzyl group transfer: two cases of aza-semipinacol-type rearrangement
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9706813/
https://www.ncbi.nlm.nih.gov/pubmed/36367325
http://dx.doi.org/10.1021/acs.orglett.2c03361
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