Related Experiment Video
Updated: Sep 19, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Distinct Selectivity of 2-Aryl Thioquinazolinones in the Sulfur Directing Rh(III)-Catalyzed Amidation Reaction
Keunju Park1, Jeonghyun Min1, Anand Kumar1
1School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
Abstract:
Sulfur-directed C-H functionalization of N-heterocycles has emerged as an alternative solution to weakly coordinating carbonyl directing groups. In this study, we describe a sulfur-promoted Rh(III)-catalyzed C5 amidation of 4-thioquinazolinones using dioxazolones, yielding 5-amido-4-thioquinazolinones. The synthetic utility was demonstrated through a gram-scale experiment and synthetic modifications of the title compounds. A series of mechanistic investigations, including competition experiments, elucidated the effectiveness of the sulfur directing group in this process.
Related Concept Videos
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation and Reactions of Thiols
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Nucleophilic Aromatic Substitution: Elimination–Addition
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

