Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives

[Image: see text] A concise, metal-free, and gram-scale strategy to convert indoline-2,3-diones to 1,2,4-oxadiazole[4,5-a]indolones through an improved [3 + 2] cycloaddition of α-ketone-lactam with nitrile oxides has been developed. The lactim form of the resonance structure of isatin in protic solv...

Descripción completa

Detalles Bibliográficos
Autores principales: Jiang, Kun-Ming, Luesakul, Urarika, Zhao, Shu-Yue, An, Kun, Muangsin, Nongnuj, Neamati, Nouri, Jin, Yi, Lin, Jun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044867/
https://www.ncbi.nlm.nih.gov/pubmed/30023685
http://dx.doi.org/10.1021/acsomega.7b00490
_version_ 1783339560961310720
author Jiang, Kun-Ming
Luesakul, Urarika
Zhao, Shu-Yue
An, Kun
Muangsin, Nongnuj
Neamati, Nouri
Jin, Yi
Lin, Jun
author_facet Jiang, Kun-Ming
Luesakul, Urarika
Zhao, Shu-Yue
An, Kun
Muangsin, Nongnuj
Neamati, Nouri
Jin, Yi
Lin, Jun
author_sort Jiang, Kun-Ming
collection PubMed
description [Image: see text] A concise, metal-free, and gram-scale strategy to convert indoline-2,3-diones to 1,2,4-oxadiazole[4,5-a]indolones through an improved [3 + 2] cycloaddition of α-ketone-lactam with nitrile oxides has been developed. The lactim form of the resonance structure of isatin in protic solvents is the key active dipolarophile that shows chemo- and regioselectivity under experimental and theoretical conditions. This strategy conveniently enabled the assembly of several 1,2,4-oxadiazole[4,5-a]indolines with a broad range of functional groups. Compounds 3a and 4b exhibit cytotoxicity in the NCI/ADR-RES, SKOV3, and OVCAR8 cell lines.
format Online
Article
Text
id pubmed-6044867
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60448672018-07-16 Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives Jiang, Kun-Ming Luesakul, Urarika Zhao, Shu-Yue An, Kun Muangsin, Nongnuj Neamati, Nouri Jin, Yi Lin, Jun ACS Omega [Image: see text] A concise, metal-free, and gram-scale strategy to convert indoline-2,3-diones to 1,2,4-oxadiazole[4,5-a]indolones through an improved [3 + 2] cycloaddition of α-ketone-lactam with nitrile oxides has been developed. The lactim form of the resonance structure of isatin in protic solvents is the key active dipolarophile that shows chemo- and regioselectivity under experimental and theoretical conditions. This strategy conveniently enabled the assembly of several 1,2,4-oxadiazole[4,5-a]indolines with a broad range of functional groups. Compounds 3a and 4b exhibit cytotoxicity in the NCI/ADR-RES, SKOV3, and OVCAR8 cell lines. American Chemical Society 2017-07-03 /pmc/articles/PMC6044867/ /pubmed/30023685 http://dx.doi.org/10.1021/acsomega.7b00490 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Jiang, Kun-Ming
Luesakul, Urarika
Zhao, Shu-Yue
An, Kun
Muangsin, Nongnuj
Neamati, Nouri
Jin, Yi
Lin, Jun
Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives
title Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives
title_full Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives
title_fullStr Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives
title_full_unstemmed Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives
title_short Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives
title_sort tautomeric-dependent lactam cycloaddition with nitrile oxide: facile synthesis of 1,2,4-oxadiazole[4,5-a]indolone derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044867/
https://www.ncbi.nlm.nih.gov/pubmed/30023685
http://dx.doi.org/10.1021/acsomega.7b00490
work_keys_str_mv AT jiangkunming tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT luesakulurarika tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT zhaoshuyue tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT ankun tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT muangsinnongnuj tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT neamatinouri tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT jinyi tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives
AT linjun tautomericdependentlactamcycloadditionwithnitrileoxidefacilesynthesisof124oxadiazole45aindolonederivatives

Ejemplares similares