title: Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin.
abstract: 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).
authors.affiliation: Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University , 26 Pildong 3-ga, Jung-gu, Seoul 100-715, Korea.
authors.forename: Seul-Gi
authors.initials: SG
authors.lastname: Kim
authors.forename: Se-Lin
authors.initials: SL
authors.lastname: Jung
authors.forename: Gee-Hyung
authors.initials: GH
authors.lastname: Lee
authors.forename: Young-Dae
authors.initials: YD
authors.lastname: Gong
mesh_terms: D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D003500:Cyclization; D015394:Molecular Structure; D012117:Resins, Synthetic / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D013890:Thiourea / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D052160:Benzothiazoles; D012117:Resins, Synthetic; D013890:Thiourea