Solid phase synthesis of 2-aminobenzothiazoles.
A traceless solid supported protocol for the synthesis of 2-aminobenzothiazoles is described, employing resin-bound acyl-isothiocyanate and a series of anilines. Cyclization of the resulting N-acyl, N'-phenyl-thioureas generates the 2-aminobenzothiazole scaffold, which can be further elaborated prior to hydrazine-mediated cleavage of the final products from the carboxy-polystyrene resin. A small, focused library of 2-aminobenzothiazoles was prepared.
Piscitelli
Francesco
F
Department of Chemistry, University of Pennsylvania, 231 South 34th St., Philadelphia, PA 19104-6323, United States.
Ballatore
Carlo
C
Smith
Amos B
AB
D000814:Aniline Compounds / Q000737:chemistry; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006834:Hydrazines / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry; D008968:Molecular Conformation; D013890:Thiourea / Q000737:chemistry
D000814:Aniline Compounds; D052160:Benzothiazoles; D006834:Hydrazines; D017879:Isothiocyanates; C523775:aminobenzothiazole compound; C029424:hydrazine; C037152:isothiocyanic acid; D013890:Thiourea; C023650:aniline