Recent Functionalizations of Primary Sulfonamides

Abstract

Sulfonamides are common building blocks in organic synthesis. They have a wide range of medical applications. This review aims to delineate recent efforts towards the functionalization of primary sulfonamides during last three years and to provide an overview of the synthesis of N-alkylated, N-acylated, and N-arylated sulfonamides from primary sulfonamides. Among other reactions, the sulfonamide-directed C-H functionalization is highlighted.

Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System

“…The toxicity of the starting materials and the need for a stoichiometric quantity of a base render this process less attractive from the point of view of atom‐economy and safety. Consequently, other routes have been widely investigated . Among these alternatives, N ‐alkylation of sulfonamides with benzylic alcohols has gained great attention from the organic chemistry community .…”

Regioselective reaction of imidazole-2-thiols with N-sulfonylphenyldichloroacetaldimines: en route to novel sulfonylamino-substituted imidazo[2,1-b]thiazoles and thiazolo[3,2-a]benzimidazoles

“…50 Sulfonamides are widely used in organic syntheses. [51][52][53][54][55] A sulfonamide fragment can be regarded as a protected amino group. 56,57 Thus, importance of the sulfonamide compounds for modern medicine and organic synthesis can hardly be overestimated.…”

Acid-base properties of imidazo[2,1-<i>b</i>] tiazole and tiazolo[3,2-<i> а</i>] benzimidazole derivatives

“…Эти соединения проявляют противоопухолевое [3], противомикробное [4], противо-диабетическое [5], мочегонное [6], противоглистное [7] и фунгицидное [8] свойства. Таким образом, разработка эффективных методов получения замещенных имидазо[2,1-b]тиазолов, а также синтез новых представителей гетероциклических систем напрямую связаны с возможностью создания лекарственных препаратов [9][10][11][12][13][14], что является актуальной задачей. Не менее важным является изучение NH-кислотности этих соединений, поскольку на основании данных о кислотно-основных свойствах соединений можно предвидеть некоторые их физико-химические свойства и реакционную способность.…”