Sultams: Recent Syntheses and Applications

Abstract

Sultams are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry. Very important methodologies for the asymmetric and non‐asymmetric synthesis of sultams, including asymmetric synthesis with memory of chirality (MOC), have recently been developed. Nowadays sultams are tremendously widely applied both in the medicinal field and in the synthetic field for the synthesis of different natural and non‐natural heterocycles. This review covers the recent development (2011–June 2017) of powerful methodologies for the synthesis of sultams and their applications in various fields during this period. A critical view of the mechanisms of the developed methodologies together with the scope and limitations of these methods add an extra dimension to the text.

Recent Advances in Catalytic Synthesis of Benzosultams

“…For instance, Sundararaju and Volla et al independently developed Co-catalyzed C−H activation/N−H cyclization of sulfonamides with the use of alkynes or allenes as coupling partners, yielding a variety of biologically interesting benzosultam motifs [ 63 , 64 ]. These works have been covered in a previous review, which were not discussed in detail here [ 41 ].…”

“…Taking advantage of the high and unique reactivity of free radicals, the radical-induced synthetic strategy has also been applied to construct 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 ].…”

Ring closing metathesis strategies to isoxazole containing thiadiazepines

“…This facilitated the development of drugs for the treatment of glaucoma [6], epilepsy [7], arthritis [8], osteoporosis [9], Alzheimer's disease [10], cancer [11], and others. Cyclic sulfamides are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry [12], among of them, have been found substances that have proven themselves as peptidomimetics, in particular, HIV-proteinase inhibitors [13], [14]. Thus, in particular, N, N'disubstituted derivatives of thiodiazepines were active inhibitors of HIV-1 proteinase [15], [16].…”

A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides

“…Whereas the introductiono fasulfonamidem oiety on small molecules is relativelye asy and well-established, [3] the development of synthetic approachesa ffording ar ange of diverse biologically relevant cyclic sulfonamides remain underexplored. [4] Herein, we disclose as caffold-diversity synthesis of cyclic benzo-sulfonamidesbyemploying asequential "branching-folding" synthetic approacha nd using easily accessible saccharin-derived cyclic N-sulfonyl ketimines 1 as the precursors(Scheme 1c). [5] In this approach, the first branching pathway exploits differenta nnulation and nucleophilic addition reactions on commons ubstrates to form complex and cyclic sulfonamides with more sp 3 character and decorated with stereogenic centers.…”