title: Electrophilic alpha-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones.
abstract: Electrophilic alpha-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. Alpha-thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.
authors.affiliation: Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390, USA. j.falck@UTSouthwestern.edu
authors.forename: J R
authors.initials: JR
authors.lastname: Falck
authors.forename: Shuanhu
authors.initials: S
authors.lastname: Gao
authors.forename: Ravi Naga
authors.initials: RN
authors.lastname: Prasad
authors.forename: Sreenivasulu Reddy
authors.initials: SR
authors.lastname: Koduru
mesh_terms: D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D045162:Thiazolidinediones / Q000737:chemistry*; D013861:Thiocyanates
chemical_list: D007094:Imides; D045162:Thiazolidinediones; D013861:Thiocyanates; C089946:2,4-thiazolidinedione