Synthesis of 2-thio- and 2-oxoimidazoles via cascade addition-cycloisomerization reactions of propargylcyanamides.
A methodology to generate 2-thio- and 2-oxoimidazoles through an addition-cyclization-isomerization reaction of propargylcyanamides with thiol and alcohol nucleophiles is described. In general, the reaction sequence allows for the rapid formation of highly substituted 2-thio- and 2-oxoimidazoles in good to excellent yields.
Giles
Robert L
RL
Department of Chemistry, University of Utah, 315 South 1400 East, Salt lake City, Utah 84112, USA.
Nkansah
Richard A
RA
Looper
Ryan E
RE
D000480:Alkynes / Q000737:chemistry; D003484:Cyanamide / Q000737:chemistry*; D003500:Cyclization; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010293:Pargyline / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D013438:Sulfhydryl Compounds; D003484:Cyanamide; D010293:Pargyline