Recent Advances in Catalytic Synthesis of Benzosultams

Abstract

Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.

Sulfoxylate Anion Radical-Induced Aryl Radical Generation and Intramolecular Arylation for the Synthesis of Biarylsultams

“…To further expand the scope of aryl radical generation induced by SO 2 –• and subsequent reactions of aryl radicals in biaryl synthesis, we embarked on the synthesis of biaryls embedded in cyclic sulfonamide frameworks (biarylsultams) that represent an important structural motif, a privileged scaffold in drug discovery, and drug-like pharmaceuticals. Although various synthetic approaches have been developed in the past decades, − the preparative complexity of biarylsultams, our on-going interest on biarylsultams, , and the quest for an efficient and convergent synthetic approach have captivated our attention for further exploring SO 2 –• - induced aryl radical generation and subsequent intramolecular reactions in biaryl synthesis. Toward this endeavor, we have developed a greener and practical approach to synthesize diverse biarylsultams via SO 2 –• -induced intramolecular C­(sp)–H arylation of easily accessible 2-bromo-arylsulfonamides.…”

Water enables diastereodivergency in bispidine-based chiral amine-catalyzed asymmetric Mannich reaction of cyclic N-sulfonyl ketimines with ketones

“…Chiral benzosultams are important compounds possessing interesting biological activities, such as γ-secretase inhibitors, HIV-1 inhibitors and aldose reductase inhibitors ( Scheme 1 ). 9 Among all the synthetic methods, 10 the catalytic asymmetric reactions about cyclic N -sulfonyl ketimines are undoubtedly one of the most convenient and atom-economic one. Up to now, many asymmetric methodologies, including Mannich reaction, 11 aza-Friedel–Crafts reaction, 12 annulation, 13 C(sp 3 )–H functionalization reaction, 14 addition of organometallic reagents 15 or unsaturated hydrocarbons 16 to imines and so on, 17 have been developed to synthesize various functionalized chiral benzosultams.…”

Intramolecular Arylation of 2‐Bromobenzenesulfonamides Using DMSO/HCOONa ⋅ 2H2O System: An Access To Dibenzosultams

“…Among them, dibenzosultams have been found to exhibit important biological and medicinal activities. [1] For example, carbapenem-derived dibenzosultams provide for potent binding to the traget penicillin binding proteins (PBPs), showing good antibiotic activity against resistant gram-positive bactieria. [2] The quinoline-fused dibenzosultams are capable of regulating nuclear factor-kB (NF-kB) pathway, which are disclosed as a favorable target for treating chronic inflammation and neurodegenerative diseases.…”