133171-80-9Relevant academic research and scientific papers
Electrosynthesis of sulfonamides from DMSO and amines under mild conditions
Lin, Zhiguan,Huang, Liangbin,Yuan, Gaoqing
supporting information, p. 3579 - 3582 (2021/04/14)
With DMSO as the solvent and the precursor of a -SO2Me unit at room temperature, a novel electrochemical oxidization and amination of DMSO with amines was developed for the synthesis of sulfonamides. Our investigations reveal that this transformation may involve a radical process and an electrochemical oxidization of DMSO.
Carbazole-containing sulfonamides and sulfamides: Discovery of cryptochrome modulators as antidiabetic agents
Humphries, Paul S.,Bersot, Ross,Kincaid, John,Mabery, Eric,McCluskie, Kerryn,Park, Timothy,Renner, Travis,Riegler, Erin,Steinfeld, Tod,Turtle, Eric D.,Wei, Zhi-Liang,Willis, Erik
, p. 757 - 760 (2016/05/24)
A series of novel carbazole-containing sulfonamides and sulfamides were synthesized. A structure-activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the results of efficacy studies in diet-induced obese (DIO) mice, and the desired pharmacokinetic parameters, compound 41 was selected for further profiling.
Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor
O'Sullivan, Steven,Doni, Eswararao,Tuttle, Tell,Murphy, John A.
supporting information, p. 474 - 478 (2014/01/23)
A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a)ArC-NR and b)ArN-C bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation. Radical fragmentations: Electron transfer from the photoactivated neutral electron donor 1 delivers high yields of S-N and C-N cleavage products for a range of nitrogen-containing species. These reactions proceed at room temperature and under mild reaction conditions in the absence of any metal reagents. DMF=N,N-dimethylformamide, Ts=4-toluenesulfonyl.
From ynamides to highly substituted benzo[b]furans: Gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates
Blanco Jaimes, Maria Camila,Weingand, Vanessa,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 12504 - 12511 (2013/09/23)
A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both C-O and C-C formation steps, thus providing benzofurans with amine functionalities at the 2-position and alkyl groups at the 3-position. Cross-over experiments showed that the alkyl-migration step was an intermolecular process. X-ray crystal-structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3-position were obtained as side-products, which were formed through a competing protodeauration process. Golden touch: Arylynamides with o-alkyloxy groups were prepared through an alkylation/cross-coupling/amidation sequence. Their Au-catalyzed conversion provided benzofurans with amine groups at the 2-position and alkyl groups at the 3-position. Copyright
