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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
N-Arylation of Sulfonamides on Solid Supports
1Chemical and Physical Sciences Department, DuPont Pharmaceuticals Company, Experimental Station, P.O. Box 80500, Wilmington, Delaware 19880-0500.
Journal of Combinatorial Chemistry
|May 18, 2000
Summary
A new method enables mild N-arylation of sulfonamides on solid supports using copper acetate and arylboronic acids. This approach also provides a route to N-arylated secondary amines.
Area of Science:
- Organic Chemistry
- Solid-Phase Synthesis
- Catalysis
Background:
- Sulfonamide functionalization is crucial in medicinal chemistry.
- Developing mild and efficient N-arylation methods remains an active research area.
- Solid-phase synthesis offers advantages in purification and automation.
Purpose of the Study:
- To report a general and mild method for the N-arylation of sulfonamides immobilized on solid supports.
- To explore the utility of the synthesized N-arylsulfonamides for further derivatization.
Main Methods:
- Copper acetate and triethylamine mediated coupling reaction.
- Utilizing arylboronic acids as arylation agents.
- Performing the reaction at room temperature on solid-supported sulfonamides.
Main Results:
- Achieved good to excellent yields of N-arylsulfonamides.
- Demonstrated the generality of the method for sulfonamide N-arylation.
- Successfully cleaved the sulfonamide bond to yield N-arylated secondary amines.
Conclusions:
- The developed method offers a mild and efficient route for solid-phase N-arylation of sulfonamides.
- This methodology facilitates access to valuable N-arylated secondary amine building blocks.
- The approach is suitable for combinatorial chemistry and drug discovery efforts.
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