Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin...

Descripción completa

Detalles Bibliográficos
Autores principales: Sun, Yan, Sun, Jing, Yan, Chao-Guo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566796/
https://www.ncbi.nlm.nih.gov/pubmed/23399791
http://dx.doi.org/10.3762/bjoc.9.2
_version_ 1782258602467131392
author Sun, Yan
Sun, Jing
Yan, Chao-Guo
author_facet Sun, Yan
Sun, Jing
Yan, Chao-Guo
author_sort Sun, Yan
collection PubMed
description A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.
format Online
Article
Text
id pubmed-3566796
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-35667962013-02-11 Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione Sun, Yan Sun, Jing Yan, Chao-Guo Beilstein J Org Chem Full Research Paper A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed. Beilstein-Institut 2013-01-03 /pmc/articles/PMC3566796/ /pubmed/23399791 http://dx.doi.org/10.3762/bjoc.9.2 Text en Copyright © 2013, Sun et al. 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 Full Research Paper
Sun, Yan
Sun, Jing
Yan, Chao-Guo
Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
title Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
title_full Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
title_fullStr Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
title_full_unstemmed Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
title_short Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
title_sort synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566796/
https://www.ncbi.nlm.nih.gov/pubmed/23399791
http://dx.doi.org/10.3762/bjoc.9.2
work_keys_str_mv AT sunyan synthesisofspirodihydropyridineoxindolesviathreecomponentreactionofarylamineisatinandcyclopentane13dione
AT sunjing synthesisofspirodihydropyridineoxindolesviathreecomponentreactionofarylamineisatinandcyclopentane13dione
AT yanchaoguo synthesisofspirodihydropyridineoxindolesviathreecomponentreactionofarylamineisatinandcyclopentane13dione

Ejemplares similares