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A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues

Arno Verlee UGent, Thomas Heugebaert UGent, Tom van der Meer UGent, Pavel Kerchev, Frank Van Breusegem UGent and Christian Stevens UGent (2017) BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 13. p.303-312
abstract
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ACTIVE PHARMACEUTICAL INGREDIENTS, CONTINUOUS-FLOW PROCESS, CHEMISTRY, SAFE, PERSPECTIVE, DERIVATIVES, INHIBITORS, POTENT, SIRT2, flow chemistry, medium-throughput synthesis, m-sulfamoylbenzamide, analogues
journal title
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Beilstein J. Org. Chem.
volume
13
pages
303 - 312
Web of Science type
Article
Web of Science id
000395045100001
ISSN
1860-5397
DOI
10.3762/bjoc.13.33
project
Biotechnology for a sustainable economy (Bio-Economy)
language
English
UGent publication?
yes
classification
A1
copyright statement
Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)
id
8516891
handle
http://hdl.handle.net/1854/LU-8516891
date created
2017-04-04 13:16:54
date last changed
2017-05-05 12:45:08
@article{8516891,
  abstract     = {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.},
  author       = {Verlee, Arno and Heugebaert, Thomas and van der Meer, Tom and Kerchev, Pavel and Van Breusegem, Frank and Stevens, Christian},
  issn         = {1860-5397},
  journal      = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {ACTIVE PHARMACEUTICAL INGREDIENTS,CONTINUOUS-FLOW PROCESS,CHEMISTRY,SAFE,PERSPECTIVE,DERIVATIVES,INHIBITORS,POTENT,SIRT2,flow chemistry,medium-throughput synthesis,m-sulfamoylbenzamide,analogues},
  language     = {eng},
  pages        = {303--312},
  title        = {A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues},
  url          = {http://dx.doi.org/10.3762/bjoc.13.33},
  volume       = {13},
  year         = {2017},
}

Chicago
Verlee, Arno, Thomas Heugebaert, Tom van der Meer, Pavel Kerchev, Frank Van Breusegem, and Christian Stevens. 2017. “A Chemoselective and Continuous Synthesis of M-sulfamoylbenzamide Analogues.” Beilstein Journal of Organic Chemistry 13: 303–312.
APA
Verlee, Arno, Heugebaert, T., van der Meer, T., Kerchev, P., Van Breusegem, F., & Stevens, C. (2017). A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 13, 303–312.
Vancouver
1.
Verlee A, Heugebaert T, van der Meer T, Kerchev P, Van Breusegem F, Stevens C. A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2017;13:303–12.
MLA
Verlee, Arno, Thomas Heugebaert, Tom van der Meer, et al. “A Chemoselective and Continuous Synthesis of M-sulfamoylbenzamide Analogues.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 13 (2017): 303–312. Print.