69139-08-8Relevant academic research and scientific papers
Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes
Bandaru, Siva Sankar Murthy,Bhilare, Shatrughn,Cardozo, Jesvita,Chrysochos, Nicolas,Schulzke, Carola,Sanghvi, Yogesh S.,Gunturu, Krishna Chaitanya,Kapdi, Anant R.
, p. 8921 - 8940 (2019/07/08)
The thioetherification of heteroaryl chlorides is an essential synthetic methodology that provides access to bioactive drugs and agrochemicals. Due to their (actual or potential) industrial importance, the development of efficient and low-temperature protocols for accessing these compounds is a requirement for economic and ecologic reasons. A particular highly effective catalytic protocol using the Pd/PTABS system at only 50 °C was developed accordingly. The coupling between chloroheteroarenes and a variety of less reactive arylthiols and alkylthiols was carried out with a high efficiency. Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.
REDUCTIVE DEBROMINATION OF 5-BROMOURACILS BY 1-BENZYL-1,4-DIHYDRONICOTINAMIDE
Sako, Magoichi,Hirota, Kosaku,Maki, Yoshifumi
, p. 3919 - 3922 (2007/10/02)
N(1)-Unsubstituted 5-bromouracils with or without a substituent in position 6 undergo reductive debromination with ease most likely via a one-electron transfer process upon treatment with 1-benzyl-1,4-dihydronicotinamide under thermal conditions.
Reductive Debromination and Coupling Reaction in the Thermolysis of 5-Bromouracils in N,N-Dialkylamides. Cleavage of the C(5)-Bromine bond by an Initial Electron-transfer Process
Sako, Magiochi,Suzuki, Mikio,Tanabe, Miyuki,Maki, Yoshifumi
, p. 3114 - 3117 (2007/10/02)
Thermolysis of various 5-bromouracils (1) in N,N-dialkylamides results in the formation of methylenebisuracils (2) and reductive debrominated products (3) via cleavage of the C(5)-Br bond; the latter involves a one-electron transfer process.The product distribution between (2) and (3) depends upon the nature of substituents in the uracil ring.
Synthesis and Properties of 1-Benzothiopyranopyrimidine-2,4-(3H)diones (10-Thia-5-deazaflavins)
Yoneda, Fumio,Tsukuda, Kinshiro,Kawazoe, Michiko,Sone, Atsuko,Koshiro, Akira
, p. 1329 - 1334 (2007/10/02)
Treatment of 6-arylthiouracils with the Vilsmeier reagent (dimethylformamide-phosphorus oxychloride) gave the corresponding 6-arylthio-5-formyluracils, which could alternatively be prepared by the condensation of 6-chloro-5-formyluracils with thiophenols.Dehydrative cyclization of the above 5-formyluracils with polyphosphoric acid gave 1-benzothiopyranopyrimidine-2,4-(3H)diones (10-thia-5-deazaflavins).These 10-thia-5-deazaflavins oxidized alcohols to give the corresponding carbonyl compounds with the aid of strong base, and they were hydrogenated to 1,5-dihydro-10-thia-5-deazaflavins.Treatment of 10-thia-5-deazaflavins with the concentrated aqueous potassium hydroxide led to the exclusive formation of 1,5-dihydro-10-thia-5-deazaflavins and 1,5-dihydro-10-thia-5-deazaflavins-5-ones via intermolecular oxidation-reduction (disproportionation) between initially formed 1,5-dihydro-5-hydroxy-10-thia-5-deazaflavins and unchanged 10-thia-5-deazaflavins.
