TY - JOUR
T1 - 1,3-Heterazolidines-2-heterounsaturated compounds derived from ephedrines
AU - Cruz, Alejandro
AU - Contreras, Rosalinda
AU - Padilla-Martínez, Itzia I.
AU - Juárez-Juárez, Minerva
N1 - Funding Information:
The authors thank Conacyt-México (Grant 32190-E) and Coordinación General de Posgrado e Investigación-IPN for financial support.
PY - 2006/6/19
Y1 - 2006/6/19
N2 - Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180-200 °C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochemistry of the compounds were determined by 1H, 13C NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction.
AB - Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180-200 °C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochemistry of the compounds were determined by 1H, 13C NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction.
UR - http://www.scopus.com/inward/record.url?scp=33745338602&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2006.05.009
DO - 10.1016/j.tetasy.2006.05.009
M3 - Artículo
SN - 0957-4166
VL - 17
SP - 1499
EP - 1505
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 10
ER -