Novel Solid-Phase Parallel Synthesis of N-Substituted-2-aminobenzo [d]thiazole Derivatives via Cyclization Reactions of 2-Iodophenyl Thiourea Intermediate Resin
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- 作者：Seul-Gi Kim ; Se-Lin Jung ; Gee-Hyung Lee ; Young-Dae Gong
- 刊名：ACS Combinatorial Science
- 出版年：2013
- 出版时间：January 14, 2013
- 年：2013
- 卷：15
- 期：1
- 页码：29-40
- 全文大小：522K
- 年卷期：v.15,no.1(January 14, 2013)
- ISSN：2156-8944
文摘
A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).