3077-65-4Relevant academic research and scientific papers
S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling
Wang, Xuefeng,Yang, Min,Ye, Shengqing,Kuang, Yunyan,Wu, Jie
, p. 6437 - 6441 (2021/05/19)
Sulfuric chloride is used as the source of the -SO2- group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki-Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. This journal is
A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**
Wei, Mingjie,Liang, Dacheng,Cao, Xiaohui,Luo, Wenjun,Ma, Guojian,Liu, Zeyuan,Li, Le
supporting information, p. 7397 - 7404 (2021/02/16)
A broad-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1-hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram-scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.
One-Pot Sulfonamide Synthesis Exploiting the Palladium-Catalyzed Sulfination of Aryl Iodides
Flegeau, Emmanuel Ferrer,Harrison, Jack M.,Willis, Michael C.
supporting information, p. 101 - 105 (2015/12/26)
Aryl ammonium sulfinates, conveniently prepared from aryl iodides and the sulfur dioxide surrogate DABSO, under the action of a palladium(0) catalyst, are transformed in a one-pot process to a variety of functionalized sulfonamides. The sulfinate to sulfonamide transformation is achieved by simple treatment with an aqueous solution of the relevant amine and sodium hypochlorite (bleach). A broad range of amines, including anilines, and amino acid derivatives, are combined efficiently with a variety of aryl iodides, leading to sulfonamides in high yields.
Synthesis and Biological Evaluation of Polar Functionalities Containing Nitrodihydroimidazooxazoles as Anti-TB Agents
Yempalla, Kushalava Reddy,Munagala, Gurunadham,Singh, Samsher,Kour, Gurleen,Sharma, Shweta,Chib, Reena,Kumar, Sunil,Wazir, Priya,Singh,Raina, Sushil,Bharate, Sonali S,Khan, Inshad Ali,Vishwakarma, Ram A.,Singh, Parvinder Pal
supporting information, p. 1059 - 1064 (2015/10/20)
Novel polar functionalities containing 6-nitro-2,3-dihydroimidazooxazole (NHIO) analogues were synthesized to produce a compound with enhanced solubility. Polar functionalities including sulfonyl, uridyl, and thiouridyl-bearing NHIO analogues were synthes
Practical sulfonylation of amines with 4-hydroxybenzenesulfonyl chloride: In situ silylation-desilylation
Levin, Jeremy I.,Du, Mila T.,Park, Kaapjoo
, p. 2773 - 2781 (2007/10/03)
A one-pot procedure for the efficient sulfonylation of amines with 4-hydroxybenzenesulfonyl chloride involving in situ protection and deprotection of the phenol with N,O-bis(trimethylsilyl)acetamide (BTSA) is presented.
