New Synthesis of β-Sultams from Pentafluorophenyl Sulfonates

Abstract

A stereoselective one-pot synthesis of substituted 1,2-thiazetidine 1,1-dioxides (beta-sultams) has been achieved from heterocyclic pentafluorophenyl (PFP) sulfonates. Mild N-O bond cleavage of isoxazolidines followed by intramolecular cyclization of the amine onto the PFP demonstrates the potential utility for using the PFP sulfonate as a valuable precursor to sulfonamides. [reaction: see text].

Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions

“…Recently, β-sultams have received much attention in both synthetic and medicinal chemistry [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ], mainly because of their outstanding biological activities as, for example, antibiotics and enzyme inhibitors [ 9 , 10 , 11 , 12 , 13 ]. As a result, many synthetic methods to β-sultams have been developed [ 14 , 15 , 16 , 17 ]. Among them, the most promising is the sulfa-Staudinger cycloaddition [ 18 , 19 , 20 , 21 , 22 , 23 , 24 ], which is referred to as the [2 s + 2 i ] annulation between sulfenes (or their equivalents) with imines, because of the rich and diverse sources of the starting materials.…”

Evaluation of Sulfonamide Derivatives of Dagenan Chloride as Lipoxygenase and α-Glucosidase Inhibitors

“…The first sulfonamide which was identified as the active in vivo metabolite of red azo dye was prontosil [1][2][3]. In addition, sulfonamides are known to inhibit various enzymes such as carbonic anhydrase [4]. Sulfonamides due to their resemblance to paminobenzoic acid (PABA), act as competitive inhibitors and so block the synthesis of tetrahydrofolic acid required by bacteria for growth [3,5].…”

A Simple and One‐Pot Synthesis of β‐Sultams by Using the Vilsmeier Reagent

“…To synthesize β‐sultams, a number of methods has been developed , most notably (a) cyclization of 2‐aminosulfonyl halides ; (b) cyclization of activated β‐hydroxysulfonamides ; (c) cyclization of α‐(halomethylsulfonamido) ketones, esters, or nitriles ; (d) [2 + 2] cycloaddition reactions of sulfonylamines with particularly electron‐rich olefins ; (e) ring contraction of five‐membered rings of pentafluorophenyl sulfonates ; and (f) [2 + 2] cycloaddition reactions of sulfenes with imines . Among these methods, a widely used method is via the [2 + 2] cyclocondensation of nucleophilic imines and sulfenes.…”