78096-47-6Relevant academic research and scientific papers
Microwave-Enhanced On-Water Amination of 2-Mercaptobenzoxazoles to Prepare 2-Aminobenzoxazoles
Tankam, Theeranon,Srisa, Jakkrit,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 11936 - 11943 (2018)
In this work, we developed a catalyst-free amination of 2-mercaptobenzoxazoles on water under microwave irradiation. The product, 2-aminobenzoxazoles, was successfully produced via direct amination with various amines in moderate to high yields. The formal synthesis of Suvorexant, a medication for the treatment of insomnia, was accomplished using a developed amination process. The reaction was completed in an hour at 100-150 °C in a microwave reactor without the use of external catalyst or additive. Key benefits of this process include an on-water reaction, short reaction time, being scalable and catalyst-free, and use of 2-mercaptobenzoxazoles as an inexpensive starting material having low environmental impact in its preparation.
Organocatalytic Visible Light Enabled SNAr of Heterocyclic Thiols: A Metal-Free Approach to 2-Aminobenzoxazoles and 4-Aminoquinazolines
Rattanangkool, Eakkaphon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 13256 - 13262 (2017/12/26)
The direct amination reaction of heterocyclic thiols has been developed in the presence of the nonhazardous photocatalyst Rose Bengal under irradiation of visible light. The reaction provides a straightforward approach to pharmaceutically and synthetically useful 2-aminobenzoxazole and 4-aminoquinazoline derivatives from the corresponding heterocyclic thiols with amines in good to excellent yields. Our photochemical reaction can be successfully adapted into a continuous flow reactor which is applicable for large-scale chemical industry. The key benefits of this reaction include the use of metal-free, low-cost Rose Bengal catalyst and practical operation (ambient temperature, open flask, and undried solvents).
