TY - JOUR
T1 - Efficient synthesis of cis-thiazolidinethiones derived from ephedrines
AU - Cruz, Alejandro
AU - Padilla-Martínez, Itzia I.
AU - García-Báez, Efrén V.
N1 - Funding Information:
A.C. thanks Secretaría de Investigación y Posgrado del IPN , Grant SIP-20090455 , for financial support.
PY - 2011/2/24
Y1 - 2011/2/24
N2 - The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 °C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The 1H and 13C NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed.
AB - The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 °C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The 1H and 13C NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed.
UR - http://www.scopus.com/inward/record.url?scp=79953719647&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2011.02.016
DO - 10.1016/j.tetasy.2011.02.016
M3 - Artículo
SN - 0957-4166
VL - 22
SP - 394
EP - 398
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 4
ER -