87708-00-7Relevant academic research and scientific papers
1,3-DIPOLAR CYCLOADDITION OF THIAZOLIUM N-PHENYLIMIDES WITH ACRYLONITRILE
Hirano, Hiroshi,Sugiyama, Kazuaki,Yamashita, Mayumi,Inoue, Masatoshi,Ishida, Toshimasa
, p. 1792 - 1795 (2007/10/02)
3-Anilinothiazolium salt(1) was synthesized via three steps from ammonium 3-phenyldithiocarbazate, and the cycloaddition reaction of the ylide(2) prepared from 1 with acrylonitrile was carried out in two different solvents, DMF and methanol.The reaction in DMF produced two compounds, derivatives of 2,3,3a,8b-tetrahydro-4H-2,4-ethanothiazoloindole (3a and 3b), while the similar reaction in methanol unexpectedly gave bis(4,5-dimethyl-2-thiazolyl)cyanomethane (5).The structures of 3a and 3b were established by the 1H-NMR (400 MHz) spectral data and the X-ray analysis.KEYWORDS - 1,3-dipolar cycloaddition; thiazolium N-phenylimide; 2,3,3a,8b-tetrahydro-4H-2,4-ethanothiazoloindole; 1H-NMR (400 MHz); X-ray analysis; sigmatropic rearrangement; bis(4,5-dimethyl-2-thiazolyl)cyanomethane
