5457-98-7Relevant 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.
HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines
Bhujabal, Yuvraj B.,Vadagaonkar, Kamlesh S.,Gholap, Aniket,Sanghvi, Yogesh S.,Dandela, Rambabu,Kapdi, Anant R.
, p. 15343 - 15354 (2019/12/04)
A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.
Antimycobacterial Agents. 1. Thio Analogues of Purine
Pathak, Ashish K.,Pathak, Vibha,Seitz, Lainne E.,Suling, William J.,Reynolds, Robert C.
, p. 273 - 276 (2007/10/03)
Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)-9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 μg/mL respectively against the Mtb H37Rv strain. N9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.
Synthesis of 9--adenine and -guanine
Kaiwar, Vijay,Reese, Colin B.,Gray, Emily J.,Neidle, Stephen
, p. 2281 - 2288 (2007/10/02)
2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50percent yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in ca. 40percent overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b.The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60percent yield.The former product 22 was converted in three steps and in 39percent overall yield into 9-adenine 6, and the latter product was converted in four steps and in 42percent overall yield into 9-guanine 7.X-Ray crystallographic data relating to compounds 22 and 24 are also reported.
