A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones

CsOH·H(2)O-catalyzed formal [3 + 3] cycloadditions of allenyl imide with β-ketoesters, 1,3-diketones or β-ketonitriles for the synthesis of tetrasubstituted 2-pyrone derivatives have been demonstrated. The allenyl imide was utilized as a C3-synthon, and a ketenyl intermediate was proposed via the pr...

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Autores principales: Wang, Yu-Hao, Zhang, De-Hua, Cao, Ze-Hun, Li, Wang-Lai, Huang, Yi-Yong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695344/
https://www.ncbi.nlm.nih.gov/pubmed/35423364
http://dx.doi.org/10.1039/d0ra10686k
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author Wang, Yu-Hao
Zhang, De-Hua
Cao, Ze-Hun
Li, Wang-Lai
Huang, Yi-Yong
author_facet Wang, Yu-Hao
Zhang, De-Hua
Cao, Ze-Hun
Li, Wang-Lai
Huang, Yi-Yong
author_sort Wang, Yu-Hao
collection PubMed
description CsOH·H(2)O-catalyzed formal [3 + 3] cycloadditions of allenyl imide with β-ketoesters, 1,3-diketones or β-ketonitriles for the synthesis of tetrasubstituted 2-pyrone derivatives have been demonstrated. The allenyl imide was utilized as a C3-synthon, and a ketenyl intermediate was proposed via the process of 1,4-addition of carbon anion to allene followed by elimination of the 2-oxazolidinyl group.
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spelling pubmed-86953442022-04-13 A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones Wang, Yu-Hao Zhang, De-Hua Cao, Ze-Hun Li, Wang-Lai Huang, Yi-Yong RSC Adv Chemistry CsOH·H(2)O-catalyzed formal [3 + 3] cycloadditions of allenyl imide with β-ketoesters, 1,3-diketones or β-ketonitriles for the synthesis of tetrasubstituted 2-pyrone derivatives have been demonstrated. The allenyl imide was utilized as a C3-synthon, and a ketenyl intermediate was proposed via the process of 1,4-addition of carbon anion to allene followed by elimination of the 2-oxazolidinyl group. The Royal Society of Chemistry 2021-02-26 /pmc/articles/PMC8695344/ /pubmed/35423364 http://dx.doi.org/10.1039/d0ra10686k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wang, Yu-Hao
Zhang, De-Hua
Cao, Ze-Hun
Li, Wang-Lai
Huang, Yi-Yong
A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
title A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
title_full A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
title_fullStr A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
title_full_unstemmed A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
title_short A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
title_sort formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695344/
https://www.ncbi.nlm.nih.gov/pubmed/35423364
http://dx.doi.org/10.1039/d0ra10686k
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