Enantioselective modification of sulfonamides and sulfonamide-containing drugs via carbene organic catalysis was written by Song, Runjiang;Liu, Yingguo;Majhi, Pankaj Kumar;Ng, Pei Rou;Hao, Lin;Xu, Jun;Tian, Weiyi;Zhang, Long;Liu, Hongmei;Zhang, Xinglong;Chi, Yonggui Robin. And the article was included in Organic Chemistry Frontiers in 2021.SDS of cas: 1075-62-3 This article mentions the following:
A carbene-catalyzed method for highly enantioselective modification of sulfonamides to 3-(N-substituted)aminophthalides I [R = R1 = H, Me; RR1 = OCH2O; R2 = Ph, 4-ClC6H4, Bn, etc.; Ar = Ph, 4-O2NC6H4] was disclosed. The reaction proceeded under mild conditions with broad substrate scope, wide functional group tolerance and good to excellent yields. When multiple sulfonamides or amines were present in the same mol., the reaction occurred in a highly chemo-selective manner. Application of this method allowed for selective modification of sulfonamide-containing drug mols. to form the corresponding phthalidyl derivatives, e.g., II as potential prodrugs. Exptl. observations and DFT calculations suggested that the reaction proceeded via a stepwise addition pathway, assisted by Li+ ions or protons. Non-covalent interactions, such as cation-π interactions, play important roles in enhancing the reactivity and controlling the enantioselectivity of the reaction. In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3SDS of cas: 1075-62-3).
N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.SDS of cas: 1075-62-3