88-61-9Relevant articles and documents
Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions
Fatima, Touheeth,Duguta, Govardhan,Purugula, Venkanna,Yelike, Hemanth Sriram,Kamatala, Chinna Rajanna
, p. 1001 - 1006 (2020/07/27)
Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 in aqueous acetonitrile medium at room temperature within 1–4 h, while microwave assisted reactions took place within 1–4 min under solvent-free conditions. These observations indicate significant rate accelerations in microwave assisted reactions. which were explained due to the bulk activation of molecules induced by insitu generated high temperatures and pressures when microwaves are transmitted through reaction medium.
Divergent C-H functionalizations directed by sulfonamide pharmacophores: Late-stage diversification as a tool for drug discovery
Dai, Hui-Xiong,Stepan, Antonia F.,Plummer, Mark S.,Zhang, Yang-Hui,Yu, Jin-Quan
, p. 7222 - 7228 (2011/06/26)
Modern drug discovery is contingent on identifying lead compounds and rapidly synthesizing analogues. The use of a common pharmacophore to direct multiple and divergent C-H functionalizations of lead compounds is a particularly attractive approach. Herein, we demonstrate the viability of late-stage diversification through the divergent C-H functionalization of sulfonamides, an important class of pharmacophores found in nearly 200 drugs currently on the market, including the non-steroidal anti-inflammatory blockbuster drug celecoxib. We developed a set of six categorically different sulfonamide C-H functionalization reactions (olefination, arylation, alkylation, halogenation, carboxylation, and carbonylation), each representing a distinct handle for further diversification to reach a large number of analogues. We then performed late-stage, site-selective diversification of a sulfonamide drug candidate containing multiple potentially reactive C-H bonds to synthesize directly novel celecoxib analogues as potential cyclooxygenase-II (COX-2)-specific inhibitors. Together with other recently developed practical directing groups, such as CONHOMe and CONHC6F5, sulfonamide directing groups demonstrate that the auxiliary approach established in asymmetric catalysis can be equally effective in developing broadly useful C-H activation reactions.
Reactivity of sterically hindered aromatic sulfonic acid derivatives: VII.* hydrolysis of arenesulfonyl chlorides in aqueous acetonitrile
Rubleva,Krut'ko,Mitchenko
, p. 1006 - 1009 (2007/10/03)
Hydrolysis of sterically hindered arenesulfonyl chlorides in aqueous acetonitrile is accelerated by both electron-acceptor and some electron-donor substituents in the benzene ring. A multifactor kinetic model of the process is proposed. 1998 MAHK Hayka/Interperiodica Publishing.
