58982-96-0Relevant academic research and scientific papers
Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide
Tan, Wei,Wang, Cuihong,Jiang, Xuefeng
, p. 1234 - 1238 (2019/11/21)
We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.
Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides
Villo, Piret,Kervefors, Gabriella,Olofsson, Berit
supporting information, p. 8810 - 8813 (2018/08/17)
Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.
Reformatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents
Michael, Joseph P,De Koning, Charles B,Hosken, Gladys D,Stanbury, Trevor V
, p. 9635 - 9648 (2007/10/03)
A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-α]quinoline-4-carboxylic acids, tricylic analogues of the quinolone antibiotics, is described. Key steps in the route are a novel zinc-mediated Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thione 18, and cyclisation of the resulting diethyl pyrrolidinylidenemalonate intermediates 19 in polyphosphoric acid. The products proved to be devoid of biological activity.
A polymer-supported thionating reagent
Ley, Steven V.,Leach, Andrew G.,Storer, R.Ian
, p. 358 - 361 (2007/10/03)
A new polymer-supported reagent for the conversion of carbonyls to thiocarbonyls has been developed and its use demonstrated on a range of amides. Secondary or tertiary amides are converted cleanly and efficiently through to the corresponding thioamides and primary amides are converted to the corresponding nitriles. The reactions can be facilitated by conventional heating. However, if microwave heating is used, in the presence of an ionic liquid, enhanced reaction rates are achieved.
A versatile synthesis of tricyclic analogues of quinolone antibacterial agents: Use of a novel Reformatsky reaction
Michael, Joseph P.,De Koning, Charles B.,Stanbury, Trevor V.
, p. 9403 - 9406 (2007/10/03)
A simple synthesis of tricyclic analogues of the quinolone antibiotics bearing a diverse range of substituents on the aromatic ring is described. The key steps involve unprecedented Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thiones 8, followed by cyclisation of the resulting enaminone intermediates 9 in polyphosphoric acid.
Sulfidation of Selected Carboxylic and Carbonic Acid Amides with the (9-BBN)2S-Reagent
Koester, Roland,Kucznierz, Ralf
, p. 1081 - 1086 (2007/10/02)
The sulfidation of eight carboxylic and carbonic acid amides (A-H) with bis(1,5-cyclooctanediylboryl) sulfide (1) is described.From the aliphatic acyclic amide A and the N-substituted lactams C-E the corresponding thiocarbonyl compounds 2a and 2c-e, resp.
