title: Unprecedented one-pot chemocontrolled entry to thioxoimidazolidinones and aminoimidazolones: synthesis of kinase inhibitor leucettamine B.
abstract: A novel and highly chemoselective protocol for the construction of thioxoimidazolidinone and aminoimidazolone frameworks was explored, and the influence of the reaction conditions on product formation was studied to establish two distinct approaches for their selective formation. In this one-pot reaction, ambient temperature generally resulted in the formation of thioxoimidazolidinones, whereas microwave irradiation provided aminoimidazolones exclusively. An attempt to elucidate the observed chemoselectivity is described, and the products were confirmed by X-ray studies. One-pot synthesis toward Leucettamine B, a marine alkaloid, was achieved on the basis of this protocol.
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Manikandan
authors.initials: M
authors.lastname: Selvaraju
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
mesh_terms: D000588:Amines / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013871:Thiones / Q000737:chemistry*
chemical_list: D000588:Amines; D007093:Imidazoles; D047428:Protein Kinase Inhibitors; D013871:Thiones; C000602884:leucettamine B
keywords: chemoselectivity; domino reactions; microwave chemistry; one-pot protocol; total synthesis