Saturated Bicyclic Sultams

Abstract

Saturated bicyclic sultams represent a promising class of sp 3-rich three-dimensional scaffolds of outmost importance to organic and medicinal chemistry. In this review with 99 references, synthesis, properties, and applications of these compounds are surveyed. The literature data are categorized according to the structural types (i.e. fused, bridged, and spirocyclic compounds), as well as homologous series

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

“…Thus, saturated aminoheterocycles 19 bearing a sulfonyl fluoride group easily underwent cyclization to bridged bicyclic sultams 20 (Scheme 15, B). [175][176][177][178] A related approach to spirocyclic sultams 21 relied on the intramolecular reductive sulfonylation of cyanoalkyl sulfonyl fluorides 22 via the formation of aminoalkyl sulfonyl fluorides 23 (Scheme 15, C). [179] Another example relied on annulative SuFEx reaction of arylsubstituted ethenesulfonyl fluorides 24 as bis-electrophiles with ketones bearing an activated methylene group [180][181][182] or pyrazolones [181][182][183] for the synthesis of 6-membered δ-sultones 25 (Scheme 15D).…”

“…In this view, intramolecular SuFEx reactions can be outlined since they provide access to (bi)cyclic sultams highly relevant to medicinal chemistry. [177] Another very important application of sulfonyl fluorides is design of covalent ligands and probes for drug discovery and chemical biology. [184,185] Selected examples include Pefabloc (4-(2-aminoethyl)benzenesulfonyl fluoride, AEBFS), an irreversible serine protease inhibitor, [186,187] 5'-(4-fluorosulfonylbenzoyl)adenosine (FSBA), an ATP-binding protein inhibitor, [188,189] SF-p1yne, a clickable covalent probe for scavenger mRNA-decapping enzyme (DcpS protein), [190] or dansyl fluoride, a fluorescent specific serine-type protease inhibitor (Figure 5B).…”

Recent Advances in the Synthesis of 5‐MemberedN‐Heterocycles via Rhodium Catalysed Cascade Reactions

“…Cyclic sulfonamides (sultams) are extensively used as a chiral auxiliary in various asymmetric transformations and provided a vast spectrum of pharmaceutical properties [183a,b] . Among different types of sultams, spiro‐fused sultam derivatives present in forefront due to its high rigid structure and wide application in drug discovery.…”

Recent Advances in Catalytic Synthesis of Benzosultams

“…Mondal et al successively summarized the advances in sultam synthesis, biological activities, and synthetic applications (2000–2010, 2011–June 2017) [ 40 , 41 ]. In 2020, Grygorenko and colleagues comprehensively discussed the recent developments in the synthesis of saturated bicyclic sultams [ 42 ]. Taking into account the significance of benzosultam scaffolds, in this review, we provide an overview of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on catalytic models, substrate scopes, and reaction mechanisms.…”