22821-07-4Relevant academic research and scientific papers
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).
Preparation of 2-(3-Hydroxyalkylthio)benzoxazoles and their Conversion into Thietanes
Ikemizu, Dai,Matsuyama, Ayako,Takemura, Kazunori,Mitsunobu, Oyo
, p. 1247 - 1248 (2007/10/03)
Reaction of primary or secondary 1,3-diols with dibenzoxazol-2-yl disulfide and tributylphosphine or triphenylphosphine selectively gave 2-(3-hydroxyalkylthio)benzoxazoles which, on treatment with KH, were converted into the corresponding thietanes. 2,2-Dibenzylthietane-1-oxide reacted with silylated purines and pyrimidines in the presence of TMSOTf and ZnI2 to give the corresponding thietane nucleosides in 17-69% yields.
