期刊
ACS COMBINATORIAL SCIENCE
卷 15, 期 1, 页码 29-40出版社
AMER CHEMICAL SOC
DOI: 10.1021/co300112b
关键词
2-5 aminobenzothiazole-based libraries; solid-phase synthesis; 2-aminobenzo[d]thiazole resins; Suzuki coupling reaction
资金
- National Research Foundation of Korea [2010-0004128]
- Ministry of Education, Science and Technology
- Ministry of Knowledge Economy, Korea
- National Research Foundation of Korea [2010-0004128] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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).
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