Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence

A highly efficient one-pot procedure combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles and sub-sequent Brønsted acid-assisted spirocyclization allowed for preparation of 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically selective fashion. Utilization of alkyl Grign...

Descripción completa

Detalles Bibliográficos
Autores principales: Aksenov, Alexander V., Aksenov, Dmitrii A., Aksenov, Nicolai A., Skomorokhov, Anton A., Aleksandrova, Elena V., Rubin, Michael
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/PMC8693578/
https://www.ncbi.nlm.nih.gov/pubmed/35424118
http://dx.doi.org/10.1039/d0ra10219a
_version_ 1784619170696003584
author Aksenov, Alexander V.
Aksenov, Dmitrii A.
Aksenov, Nicolai A.
Skomorokhov, Anton A.
Aleksandrova, Elena V.
Rubin, Michael
author_facet Aksenov, Alexander V.
Aksenov, Dmitrii A.
Aksenov, Nicolai A.
Skomorokhov, Anton A.
Aleksandrova, Elena V.
Rubin, Michael
author_sort Aksenov, Alexander V.
collection PubMed
description A highly efficient one-pot procedure combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles and sub-sequent Brønsted acid-assisted spirocyclization allowed for preparation of 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically selective fashion. Utilization of alkyl Grignard reagents provided an easy access to 4′-alkylsubstituted derivatives hardly available by other means.
format Online
Article
Text
id pubmed-8693578
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-86935782022-04-13 Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence Aksenov, Alexander V. Aksenov, Dmitrii A. Aksenov, Nicolai A. Skomorokhov, Anton A. Aleksandrova, Elena V. Rubin, Michael RSC Adv Chemistry A highly efficient one-pot procedure combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles and sub-sequent Brønsted acid-assisted spirocyclization allowed for preparation of 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically selective fashion. Utilization of alkyl Grignard reagents provided an easy access to 4′-alkylsubstituted derivatives hardly available by other means. The Royal Society of Chemistry 2021-01-06 /pmc/articles/PMC8693578/ /pubmed/35424118 http://dx.doi.org/10.1039/d0ra10219a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Aksenov, Alexander V.
Aksenov, Dmitrii A.
Aksenov, Nicolai A.
Skomorokhov, Anton A.
Aleksandrova, Elena V.
Rubin, Michael
Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
title Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
title_full Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
title_fullStr Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
title_full_unstemmed Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
title_short Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
title_sort preparation of spiro[indole-3,5′-isoxazoles] via grignard conjugate addition/spirocyclization sequence
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8693578/
https://www.ncbi.nlm.nih.gov/pubmed/35424118
http://dx.doi.org/10.1039/d0ra10219a
work_keys_str_mv AT aksenovalexanderv preparationofspiroindole35isoxazolesviagrignardconjugateadditionspirocyclizationsequence
AT aksenovdmitriia preparationofspiroindole35isoxazolesviagrignardconjugateadditionspirocyclizationsequence
AT aksenovnicolaia preparationofspiroindole35isoxazolesviagrignardconjugateadditionspirocyclizationsequence
AT skomorokhovantona preparationofspiroindole35isoxazolesviagrignardconjugateadditionspirocyclizationsequence
AT aleksandrovaelenav preparationofspiroindole35isoxazolesviagrignardconjugateadditionspirocyclizationsequence
AT rubinmichael preparationofspiroindole35isoxazolesviagrignardconjugateadditionspirocyclizationsequence

Ejemplares similares