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Citation: HU Bing-Cheng, LU Chun-Xu. Synthesis of 2-Cyano-2,3-dimethyl-3-methoxycarbonyl methyl-5-thioxo-pyrrolidine[J]. Chinese Journal of Applied Chemistry, ;2004, 21(11): 1165-1168. shu

Synthesis of 2-Cyano-2,3-dimethyl-3-methoxycarbonyl methyl-5-thioxo-pyrrolidine

HU Bing-Cheng ^, ,
LU Chun-Xu

1.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: HU Bing-Cheng,
Received Date: 20 December 2003
Available Online: 30 April 2004

Amination of dimethylbicyclolactam 1 gives dimethyl-bicyclolactam-lactone 2, which transfers to cyanopyrolidones 3a and 3b through substitutive ring-opening reactions by action of hydrocyanic acid and esterification with diazomethane. Sulfidizations of 3a and 3b give the end products, cyanopyrrolidinylthiones 4a and 4b, with total yield of ca. 59%. The trans- and cis-isomeric products were isolated by HPLC in mass fraction of 64.5% and 34.0%, respectively. Their structures were confirmed by elemental analysis, UV-Vis, IR, ¹H NMR,¹³C NMR and MS spectra.
- dimethylbicyclolactam,
- dimethylbicyclolactam-lactone,
- cyanopyrrolidone,
- cyano-pyrrolidine-thione
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