A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

The synthesis of C3-carbocyclic spirooxindoles was realized by way of an intramolecular [2 + 2] cycloaddition reaction between a vinylidene indolin-2-one and an alkyne. The cycloaddition reaction occurs selectively with the distal double bond of the allene, is tolerant of a phenyl and trimethylsilyl...

Descripción completa

Detalles Bibliográficos
Autores principales: Brummond, Kay M, Osbourn, Joshua M
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874392/
https://www.ncbi.nlm.nih.gov/pubmed/20502602
http://dx.doi.org/10.3762/bjoc.6.33
_version_ 1782181472961036288
author Brummond, Kay M
Osbourn, Joshua M
author_facet Brummond, Kay M
Osbourn, Joshua M
author_sort Brummond, Kay M
collection PubMed
description The synthesis of C3-carbocyclic spirooxindoles was realized by way of an intramolecular [2 + 2] cycloaddition reaction between a vinylidene indolin-2-one and an alkyne. The cycloaddition reaction occurs selectively with the distal double bond of the allene, is tolerant of a phenyl and trimethylsilyl group on the terminus of the alkyne, and can be used to access bicyclo[4.2.0]octadienes and bicyclo[5.2.0]nonadienes. The allene precursors are not observed, but are likely intermediates of an infrequently encountered thermal [3,3]-sigmatropic rearrangement of a propargylic acetate.
format Text
id pubmed-2874392
institution National Center for Biotechnology Information
language English
publishDate 2010
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-28743922010-05-25 A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles Brummond, Kay M Osbourn, Joshua M Beilstein J Org Chem Preliminary Communication The synthesis of C3-carbocyclic spirooxindoles was realized by way of an intramolecular [2 + 2] cycloaddition reaction between a vinylidene indolin-2-one and an alkyne. The cycloaddition reaction occurs selectively with the distal double bond of the allene, is tolerant of a phenyl and trimethylsilyl group on the terminus of the alkyne, and can be used to access bicyclo[4.2.0]octadienes and bicyclo[5.2.0]nonadienes. The allene precursors are not observed, but are likely intermediates of an infrequently encountered thermal [3,3]-sigmatropic rearrangement of a propargylic acetate. Beilstein-Institut 2010-04-08 /pmc/articles/PMC2874392/ /pubmed/20502602 http://dx.doi.org/10.3762/bjoc.6.33 Text en Copyright © 2010, Brummond and Osbourn https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Brummond, Kay M
Osbourn, Joshua M
A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
title A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
title_full A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
title_fullStr A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
title_full_unstemmed A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
title_short A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
title_sort thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
topic Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874392/
https://www.ncbi.nlm.nih.gov/pubmed/20502602
http://dx.doi.org/10.3762/bjoc.6.33
work_keys_str_mv AT brummondkaym athermallyinducedtandem33sigmatropicrearrangement22cycloadditionapproachtocarbocyclicspirooxindoles
AT osbournjoshuam athermallyinducedtandem33sigmatropicrearrangement22cycloadditionapproachtocarbocyclicspirooxindoles
AT brummondkaym thermallyinducedtandem33sigmatropicrearrangement22cycloadditionapproachtocarbocyclicspirooxindoles
AT osbournjoshuam thermallyinducedtandem33sigmatropicrearrangement22cycloadditionapproachtocarbocyclicspirooxindoles

Ejemplares similares