Microwave‐assisted Solid‐phase Synthesis of N‐substituted‐2‐aminobenzo[d][1,3] Thiazine Derivatives from a BOMBA Resin

Bulletin of the Korean Chemical Society

Jeong Yoon¹  Dae Gong¹  Mi Kim¹  Goo Jun¹  Hyo‐²  Eun‐²  Young‐²  Hee‐² 

[1] 715 Korea;Center for Innovative Drug Library Research, Department of Chemistry, College of Science Dongguk University Seoul 100‐

关键词: Solid‐;    phase parallel synthesis;    Heterocycles;    Benzo[d][1,3]thiazine;    ;    BOMBA resin;   

DOI  :  10.1002/bkcs.11088

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 N‐acyl and N‐sulfonyl substituted 2‐aminobenzo[d][1,3]thiazine derivatives. The key step in this methodology is the preparation of backbone amide linker‐bound 2‐aminobenzo[d][1,3]thiazine resin through cyclization reaction between isothiocyanates and BOMBA resin under microwave irradiation. This 2‐aminobenzo[d][1,3]thiazine core skeleton resin undergoes substitution reactions with various electrophiles, such as acid halides and sulfonyl halides, to generate N‐acyl and N‐sulfonyl substituted 2‐aminobenzo[d][1,3]thiazine resins, respectively. Finally, N‐acyl and N‐sulfonyl‐substituted 2‐aminobenzo[d][1,3]thiazine derivatives are prepared in good yields and purities by cleavage of the respective resins under trifluoroacetic acid (TFA) in dichloromethane (DCM).

【 授权许可】

Unknown