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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 (UGent) , Frank Van Breusegem (UGent) and Christian Stevens (UGent)
Author
Organization
Project
Biotechnology for a sustainable economy (Bio-Economy)
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.
Keywords
ACTIVE PHARMACEUTICAL INGREDIENTS, CONTINUOUS-FLOW PROCESS, CHEMISTRY, SAFE, PERSPECTIVE, DERIVATIVES, INHIBITORS, POTENT, SIRT2, flow chemistry, medium-throughput synthesis, m-sulfamoylbenzamide, analogues

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  • Verlee et al. (2017) Beilstein Journal of Organic Chemistry 13,303.pdf
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Citation

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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.
@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},
  keywords     = {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},
}

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