A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues

For the synthesis of m-sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from m-(chlorosulfonyl)benzoyl chloride. Although a chemoselective process in batch was already reported, a continuous-flow process revea...

Descripción completa

Detalles Bibliográficos
Autores principales: Verlee, Arno, Heugebaert, Thomas, van der Meer, Tom, Kerchev, Pavel I, Van Breusegem, Frank, Stevens, Christian V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331323/
https://www.ncbi.nlm.nih.gov/pubmed/28326139
http://dx.doi.org/10.3762/bjoc.13.33
_version_ 1782511351667621888
author Verlee, Arno
Heugebaert, Thomas
van der Meer, Tom
Kerchev, Pavel I
Van Breusegem, Frank
Stevens, Christian V
author_facet Verlee, Arno
Heugebaert, Thomas
van der Meer, Tom
Kerchev, Pavel I
Van Breusegem, Frank
Stevens, Christian V
author_sort Verlee, Arno
collection PubMed
description For the synthesis of m-sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from m-(chlorosulfonyl)benzoyl chloride. Although a chemoselective process in batch was already reported, a continuous-flow process reveals an increased selectivity at higher temperatures and without catalysts. In total, 15 analogues were synthesized, using similar conditions, with yields ranging between 65 and 99%. This is the first automated and chemoselective synthesis of m-sulfamoylbenzamide analogues.
format Online
Article
Text
id pubmed-5331323
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-53313232017-03-21 A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues Verlee, Arno Heugebaert, Thomas van der Meer, Tom Kerchev, Pavel I Van Breusegem, Frank Stevens, Christian V Beilstein J Org Chem Full Research Paper For the synthesis of m-sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from m-(chlorosulfonyl)benzoyl chloride. Although a chemoselective process in batch was already reported, a continuous-flow process reveals an increased selectivity at higher temperatures and without catalysts. In total, 15 analogues were synthesized, using similar conditions, with yields ranging between 65 and 99%. This is the first automated and chemoselective synthesis of m-sulfamoylbenzamide analogues. Beilstein-Institut 2017-02-16 /pmc/articles/PMC5331323/ /pubmed/28326139 http://dx.doi.org/10.3762/bjoc.13.33 Text en Copyright © 2017, Verlee et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Verlee, Arno
Heugebaert, Thomas
van der Meer, Tom
Kerchev, Pavel I
Van Breusegem, Frank
Stevens, Christian V
A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
title A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
title_full A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
title_fullStr A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
title_full_unstemmed A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
title_short A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
title_sort chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331323/
https://www.ncbi.nlm.nih.gov/pubmed/28326139
http://dx.doi.org/10.3762/bjoc.13.33
work_keys_str_mv AT verleearno achemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT heugebaertthomas achemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT vandermeertom achemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT kerchevpaveli achemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT vanbreusegemfrank achemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT stevenschristianv achemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT verleearno chemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT heugebaertthomas chemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT vandermeertom chemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT kerchevpaveli chemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT vanbreusegemfrank chemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues
AT stevenschristianv chemoselectiveandcontinuoussynthesisofmsulfamoylbenzamideanalogues

Ejemplares similares