Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones

We report the synthesis and characterization of a variety of trans-3,4-substituted cyclopentanones and the corresponding tosylhydrazone derivatives starting with diethyl fumarate. Protection of the keto group followed by selective monohydrolysis of esters was achieved, resulting in cyclopentanones w...

Descripción completa

Detalles Bibliográficos
Autores principales: Bouhadir, Kamal H., Aleiwe, Bilal Abou, Fares, Fares A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268573/
https://www.ncbi.nlm.nih.gov/pubmed/22193210
http://dx.doi.org/10.3390/molecules17010001
_version_ 1783376317471784960
author Bouhadir, Kamal H.
Aleiwe, Bilal Abou
Fares, Fares A.
author_facet Bouhadir, Kamal H.
Aleiwe, Bilal Abou
Fares, Fares A.
author_sort Bouhadir, Kamal H.
collection PubMed
description We report the synthesis and characterization of a variety of trans-3,4-substituted cyclopentanones and the corresponding tosylhydrazone derivatives starting with diethyl fumarate. Protection of the keto group followed by selective monohydrolysis of esters was achieved, resulting in cyclopentanones with different substituents at positions 3 and 4. The tosylhydrazone derivative of each cyclopentanone intermediate was prepared in moderate to good yields. These compounds are potential precursors for functionalized methanofullerenes.
format Online
Article
Text
id pubmed-6268573
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62685732018-12-11 Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones Bouhadir, Kamal H. Aleiwe, Bilal Abou Fares, Fares A. Molecules Article We report the synthesis and characterization of a variety of trans-3,4-substituted cyclopentanones and the corresponding tosylhydrazone derivatives starting with diethyl fumarate. Protection of the keto group followed by selective monohydrolysis of esters was achieved, resulting in cyclopentanones with different substituents at positions 3 and 4. The tosylhydrazone derivative of each cyclopentanone intermediate was prepared in moderate to good yields. These compounds are potential precursors for functionalized methanofullerenes. MDPI 2011-12-22 /pmc/articles/PMC6268573/ /pubmed/22193210 http://dx.doi.org/10.3390/molecules17010001 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Bouhadir, Kamal H.
Aleiwe, Bilal Abou
Fares, Fares A.
Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
title Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
title_full Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
title_fullStr Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
title_full_unstemmed Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
title_short Facile Preparation of the Tosylhydrazone Derivatives of a Series of Racemic trans-3,4-Substituted Cyclopentanones
title_sort facile preparation of the tosylhydrazone derivatives of a series of racemic trans-3,4-substituted cyclopentanones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268573/
https://www.ncbi.nlm.nih.gov/pubmed/22193210
http://dx.doi.org/10.3390/molecules17010001
work_keys_str_mv AT bouhadirkamalh facilepreparationofthetosylhydrazonederivativesofaseriesofracemictrans34substitutedcyclopentanones
AT aleiwebilalabou facilepreparationofthetosylhydrazonederivativesofaseriesofracemictrans34substitutedcyclopentanones
AT faresfaresa facilepreparationofthetosylhydrazonederivativesofaseriesofracemictrans34substitutedcyclopentanones

Ejemplares similares