Cargando…

Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds

[Image: see text] A mild and efficient solvent-controlled, metal-free switchable 1,3-dipolar cycloaddition/ring contraction or ring expansion domino reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes has been developed. This domino reaction provided a series of aryl-substitute...

Descripción completa

Detalles Bibliográficos
Autores principales: Ramu, Gopathi, Hari Krishna, Namballa, Pawar, Gaurav, Visweswara Sastry, K. N., Nanubolu, Jagadeesh Babu, Nagendra Babu, Bathini
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644904/
https://www.ncbi.nlm.nih.gov/pubmed/31457971
http://dx.doi.org/10.1021/acsomega.8b01857
_version_ 1783437351499857920
author Ramu, Gopathi
Hari Krishna, Namballa
Pawar, Gaurav
Visweswara Sastry, K. N.
Nanubolu, Jagadeesh Babu
Nagendra Babu, Bathini
author_facet Ramu, Gopathi
Hari Krishna, Namballa
Pawar, Gaurav
Visweswara Sastry, K. N.
Nanubolu, Jagadeesh Babu
Nagendra Babu, Bathini
author_sort Ramu, Gopathi
collection PubMed
description [Image: see text] A mild and efficient solvent-controlled, metal-free switchable 1,3-dipolar cycloaddition/ring contraction or ring expansion domino reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes has been developed. This domino reaction provided a series of aryl-substituted 3-spirocyclopropyl-2-oxindoles and pyrazoloquinazolinones with excellent regio- and diastereoselectivity from common substrates under varying solvent conditions.
format Online
Article
Text
id pubmed-6644904
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-66449042019-08-27 Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds Ramu, Gopathi Hari Krishna, Namballa Pawar, Gaurav Visweswara Sastry, K. N. Nanubolu, Jagadeesh Babu Nagendra Babu, Bathini ACS Omega [Image: see text] A mild and efficient solvent-controlled, metal-free switchable 1,3-dipolar cycloaddition/ring contraction or ring expansion domino reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes has been developed. This domino reaction provided a series of aryl-substituted 3-spirocyclopropyl-2-oxindoles and pyrazoloquinazolinones with excellent regio- and diastereoselectivity from common substrates under varying solvent conditions. American Chemical Society 2018-10-01 /pmc/articles/PMC6644904/ /pubmed/31457971 http://dx.doi.org/10.1021/acsomega.8b01857 Text en Copyright © 2018 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 Ramu, Gopathi
Hari Krishna, Namballa
Pawar, Gaurav
Visweswara Sastry, K. N.
Nanubolu, Jagadeesh Babu
Nagendra Babu, Bathini
Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds
title Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds
title_full Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds
title_fullStr Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds
title_full_unstemmed Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds
title_short Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds
title_sort solvent-controlled, tunable domino reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes: a facile access to 3-spirocyclopropyl-2-oxindole and pyrazoloquinazolinone scaffolds
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644904/
https://www.ncbi.nlm.nih.gov/pubmed/31457971
http://dx.doi.org/10.1021/acsomega.8b01857
work_keys_str_mv AT ramugopathi solventcontrolledtunabledominoreactionof3ylideneoxindoleswithinsitugeneratedaaryldiazomethanesafacileaccessto3spirocyclopropyl2oxindoleandpyrazoloquinazolinonescaffolds
AT harikrishnanamballa solventcontrolledtunabledominoreactionof3ylideneoxindoleswithinsitugeneratedaaryldiazomethanesafacileaccessto3spirocyclopropyl2oxindoleandpyrazoloquinazolinonescaffolds
AT pawargaurav solventcontrolledtunabledominoreactionof3ylideneoxindoleswithinsitugeneratedaaryldiazomethanesafacileaccessto3spirocyclopropyl2oxindoleandpyrazoloquinazolinonescaffolds
AT visweswarasastrykn solventcontrolledtunabledominoreactionof3ylideneoxindoleswithinsitugeneratedaaryldiazomethanesafacileaccessto3spirocyclopropyl2oxindoleandpyrazoloquinazolinonescaffolds
AT nanubolujagadeeshbabu solventcontrolledtunabledominoreactionof3ylideneoxindoleswithinsitugeneratedaaryldiazomethanesafacileaccessto3spirocyclopropyl2oxindoleandpyrazoloquinazolinonescaffolds
AT nagendrababubathini solventcontrolledtunabledominoreactionof3ylideneoxindoleswithinsitugeneratedaaryldiazomethanesafacileaccessto3spirocyclopropyl2oxindoleandpyrazoloquinazolinonescaffolds