An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin

Bulletin of the Korean chemical society

Young-Dae Gong¹  Gee-Hyung Lee¹  Se-Lin Jung¹  Seul-Gi Kim¹ 

关键词: Solid-phase parallel synthesis;    Heterocycles;    Benzo[d]oxazole;    2-Hydroxyphenylthiourea linker;    BOMBA resin;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]- oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo- [d]oxazole resins 4 by cyclization reaction of 2-hydroxyphenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2- amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane (CH2Cl2).

【 授权许可】

Unknown