13070-07-0Relevant articles and documents
Dithio and thiono esters, LIV: Attempted synthesis of α-amino dithio esters by the bislactim ether method
Hartke,Brutsche
, p. 63 - 66 (1993)
Sulfhydrolysis of 2,5-bis(methylthio)-3,6-dihydropyrazine (5) gives rise to 2,5-piperazinedithione (8) and not to glycine dithiomethylester (6). The iminium salts 9, obtained by alkylation of 5, add H2S to form the 1,4-dialkyl 2,5-piperazinedithiones 10. 5 reacts with methyl chloroformate to give 2,5-bis(methylthio)-pyrazine (11), and with acetic anhydride to give the 1,4-dihydropyrazine 12. Sulfhydrolysis of the 6-membered and 7-membered iminium salts 14 leads to the thiolactames 15.
Expeditious microwave-assisted thionation with the system PSCl 3/H2O/Et3N under solvent-free condition
Pathak, Uma,Pandey, Lokesh Kumar,Tank, Rekha
, p. 2890 - 2893 (2008/09/19)
(Chemical Equation Presented) A novel thionation protocol for carbonyl compounds, with the system PSCl3/H2O/Et3N has been discovered. Clean, rapid, and efficient synthesis of a variety of thiocarbonyl compounds such as thioamides, thiolactams, thioketones, thioxanthones, and thioacridone can be achieved through this simple and convenient method under solventless condition with microwave irradiation.
Coupling-isomerization - N,S-ketene acetal-addition sequences - A three-component approach to highly fluorescent pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines
Schramm, Oana G.,Dediu, Nee,Oeser, Thomas,Mueller, Thomas J. J.
, p. 3494 - 3500 (2007/10/03)
Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]-azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cycloc
Mild method for the conversion of amides to thioamides
Charette, Andre B.,Grenon, Michel
, p. 5792 - 5794 (2007/10/03)
Aqueous ammonium sulfide was found to be an ideal substitute for hydrogen sulfide for the thiolysis of activated amides. High yields of the corresponding thioamides were obtained for a broad range of substrates, using two different procedures that are both operationally simple and inexpensive, as well as amenable to large-scale preparation. Preliminary results indicate that aqueous ammonium sulfide may also replace hydrogen sulfide in the synthesis of thionoesters from amides.
Conversion of Amides and Lactams to Thioamides and Thiolactams Using Hexamethyldisilathiane
Smith, D. C.,Lee, S. W.,Fuchs, P. L.
, p. 348 - 354 (2007/10/02)
Amides and lactams were converted to their corresponding thioamides and thiolactams employing a new protocol using hexamethyldisilathiane (TMS2S).Oxophilic promoters were employed to generate Vilsmeier-type intermediates, the most efficient reagents being phosphorus oxychloride, triphosgene, and oxalyl chloride.Thionation of intermediate chloro iminium ions was accomplished in situ with TMS2S.Yields were good to excellent for secondary and tertiary amides and lactams while yields for primary systems were poor.
Note on the Preparation of N,N-Disubstituted Aliphatic Thiocarboxamides, N-Substituted Thiolactames, and Aromatic Thiocarboxylates
Kantlehner, Willi,Haug, Erwin,Farkas, Michael
, p. 1582 - 1587 (2007/10/02)
Hydrogen sulfide reacts with the N,N-dimethylformamide acetal 1 to give N,N-(dimethyl)thioformamide (2a).The thioamides 2a-e and the thiolactams 2f,g are prepared by thiolysis of the nitriles 3a-g.The action of hydrogen sulfide on nitriles 5a-f affords the O-ethyl thiocarboxylates 6a-f.The preparation of the nitriles 3g and 5a-f is described.
Breakdown of Hemiorthothiamide Tetrahedral Intermediates Derived from O,N-Dimethyllactamium Tetrafluoroborates
Kaloustian, Moses K.,Nader, Randa B.
, p. 5050 - 5052 (2007/10/02)
The sulfhydrolytic cleavage of O,N-dimethylbutyrolactamium and O,N-dimethylvalerolactamium tetrafluoroborates involves C-N scission under kinetic control (61 deg C, NaSH, Ac2O, CHCl3) but C-O cleavage under thermodynamic control (27 deg C, NaSH, acetone).
