Electrophilic alpha-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones.
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.
Falck
J R
JR
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390, USA. j.falck@UTSouthwestern.edu
Gao
Shuanhu
S
Prasad
Ravi Naga
RN
Koduru
Sreenivasulu Reddy
SR
D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D045162:Thiazolidinediones / Q000737:chemistry*; D013861:Thiocyanates
D007094:Imides; D045162:Thiazolidinediones; D013861:Thiocyanates; C089946:2,4-thiazolidinedione