Regioselective synthesis of new 2-(E)-cyano(thiazolidin-2-ylidene)thiazoles.
Cyclocondensation of 2-[bis(methylthio)methylene]malononitrile (1) and cysteamine (2) afforded 2-(thiazolidin-2-ylidene)malononitrile (3). This compound on treatment with NaSH gave the corresponding thioamide derivative 4a in a regioselective manner on the basis of its single crystal X-ray diffraction analysis. Reaction of this compound with several alpha-bromocarbonyl compounds gave new 2-(E)-cyano(thiazolidin-2-ylidene)thiazoles 5a-g.
Bakavoli
Mehdi
M
Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran. mbakavoli@um.ac.ir
Beyzaie
Hamid
H
Rahimizadeh
Mohammad
M
Eshghi
Hossein
H
Takjoo
Reza
R
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D017550:Spectroscopy, Fourier Transform Infrared; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D013844:Thiazoles