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Pitak Chuawong. Sulfonamidation for the synthesis of trisubstituted arene intermediates. (). King Mongkut's University of Technology North Bangkok. Central Library. : , 2018.
Sulfonamidation for the synthesis of trisubstituted arene intermediates
Name: Pongsun Jhangthong
Organization :
Kasetsart University. Faculty of Science, and Special Research Unit for Advanced Magnetic Resonance (AMR)
Name: Pitak Chuawong
Organization :
Kasetsart University. Faculty of Science, and Special Research Unit for Advanced Magnetic Resonance (AMR)
Email :
Pitak.C@ku.ac.th
keyword:
Trisubstituted arenes
LCSH:
Sulfonamides
Abstract:
The sulfonamide group plays a significant role in medicinal chemistry and
pharmacology. The functional group appears in many commercial drugs such as Celebrex,
Azulfidine, and Gantrisin. Various synthetic approaches have been reported to access aryl
sulfonamides such as the palladium-catalyzed sulfonation of aryl iodides, one-pot synthesis
from magnesium sulfonates with DABSO, a reaction between a Grignard reagent and an Nchloroamine,
and the palladium-catalyzed chlorosulfonylation of arylboronic acids. Herein,
we reported a convenient synthesis of N-(4-amino-3-iodophenyl)-4-methylbenzenesulfonamide
and N-(4-amino-3-iodophenyl)methanesulfonamide from commercially available 4-
nitroaniline in 5 steps with an overall yield of 67%. The initial iodination reaction of 4-
nitroaniline using molecular iodine and silver sulfate afforded trisubstituted aryl iodide
intermediate. Acetylation of the amino group followed by reduction using sodium
borohydride and copper sulfate afforded arylamine intermediate. Finally, sulfonamidation
and deacetylation provided N-(4-amino-3-iodophenyl)-4-methylbenzenesulfonamide and N-
(4-amino-3-iodophenyl)methanesulfonamide in good yield. The trisubstituted arenes are the
key intermediates for the synthesis of biologically active indole derivatives using the Larock
heteroannulation reaction.
King Mongkut's University of Technology North Bangkok. Central Library
Address:
BANGKOK
Email:
library@kmutnb.ac.th
Created:
2018
Modified:
2019-07-22
Issued:
2019-07-12
บทความ/Article
application/pdf
BibliograpyCitation :
In Prince of Songkla University Faculty of Science. Pure and Applied Chemistry International Conference (PACCON 2018) (pp.OR64-OR69). Songkla : Prince of Songkla University
eng
©copyrights King Mongkut's University of Technology North Bangkok
RightsAccess:
ใช้เวลา
0.03081 วินาที
Pongsun Jhangthong
| Title | Contributor | Type |
|---|---|---|
| Sulfonamidation for the synthesis of trisubstituted arene intermediates
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Pongsun Jhangthong;Pitak Chuawong | บทความ/Article | |
| Synthesis of 2,3-diarylindole derivatives bearing sulfonamide functionality
มหาวิทยาลัยเกษตรศาสตร์ Pongsun Jhangthong | Pitak Chuawong Wanchai Pluempanupat | วิทยานิพนธ์/Thesis |
Pitak Chuawong
| Title | Contributor | Type |
|---|---|---|
| Sulfonamidation for the synthesis of trisubstituted arene intermediates
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Pongsun Jhangthong;Pitak Chuawong | บทความ/Article | |
| Synthesis of methoxy-oxacillin derivatives with different regiochemistry
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Amorn Tusanaviroon;Pitak Chuawong | บทความ/Article |