4823-23-8Relevant academic research and scientific papers
Convenient one-pot syntheses of 1,2-dithiole-3-thiones and 3-imino-1,2-dithioles from terminal alkynes
Adams, Harry,Hughes, Amelia J.,Morris, Michael J.,Quenby, Sophia I.A.
, p. 5283 - 5285 (2015/02/02)
The reaction of acetylide anions with carbon disulfide or phenyl isothiocyanate followed by addition of sulfur in the presence of a protonating agent such as a primary amine or alcohol affords 1,2-dithiole-3-thiones or 3-imino-1,2-dithioles in good to excellent yields.
The reactivity of (Z)-5-acetyl-3-aryl-2,3-dihydro-2-[(thioacyl)methylene]-1,3,4-thiadiazoles: A surprising base-induced conversion into 3-(N-arylamino)thiophenes
Benincori, Tiziana,Pilati, Tullio,Rizzo, Simona,Sada, Mara,Sannicolo, Franco
, p. 2480 - 2487 (2007/10/03)
We report the reactivity shown by two classes of rarely investigated heterocycles, the 5-acetyl-2,3-dihydro-3-phenyl-2-(phenylmethylene)-1,3,4-thiadiazoles (6) and the 5-alkanoyl-3-aryl-2,3-dihydro-2-[(thioacyl)methylene]-1,3,4-thiadiazoles 1a-e. In both cases, strong bases promote cleavage of the thiadiazole ring with loss of thiocyanate anion, generating N-arylketeneimines and N-aryl(thioacyl)keteneimines 5, respectively. These very reactive species undergo either nucleophilic addition or [4+2] cycloaddition reactions involving the thioacyl function. The most surprising result was found in the reactions of the 5-acetyl-3-aryl-2,3-dihydro-2-[(thioacyl)methylene]-1,3,4-thiadiazoles 1a,d,e, which afford 3-(arylamino)thiophenes 2, 10, and 14 as the main products. This serendipitous transformation, which seems to be rather general, probably involves an intermediate step in which the acetyl group of the substrates is converted into ketene. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
