title: Solid-Phase Synthesis of 2,3-Dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-Dioxides with Three Diversity Positions.
abstract: Synthesis of 2,3-dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-dioxides from polymer-supported α-amino acids is described herein. Different α-amino acids immobilized on Wang resin were sulfonylated with various 2-nitrobenzenesulfonyl chlorides. The resulting 2-nitrobenzenesulfonamides were alkylated with alcohols according to the Fukuyama-Mitsunobu procedure. After reduction of the nitro group and cleavage from the polymer support, the final intermediates were reacted with thionyl chloride, and target compounds of good crude purity and acceptable overall yields were obtained. The chiral HPLC studies revealed the impact of the cyclization step on the resulting stereochemistry. The developed strategy allows for simple production of desired compounds with the application of parallel/combinatorial solid-phase synthesis using commercially available building blocks.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 771 46 Olomouc, Czech Republic.
authors.forename: Patricia
authors.initials: P
authors.lastname: Trapani
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 771 46 Olomouc, Czech Republic.
authors.forename: Tereza
authors.initials: T
authors.lastname: Volná
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 771 46 Olomouc, Czech Republic.|Institute of Molecular and Translation Medicine, Faculty of Medicine and Dentistry, Palacký University , Hněvotínská 5, 779 00, Olomouc, Czech Republic.
authors.forename: Miroslav
authors.initials: M
authors.lastname: Soural
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D010087:Oxides / Q000138:chemical synthesis; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013841:Thiazepines / Q000138:chemical synthesis*
chemical_list: D000596:Amino Acids; D001555:Benzene Derivatives; D010087:Oxides; D013841:Thiazepines
keywords: 2-nitrobenzenesulfonyl chlorides; Fukuyama−Mitsunobu alkylation; solid-phase synthesis; thiadiazepin-4(5H)-one 1,1-dioxides