Synthesis, Characterization, and Antimicrobial Evaluation of Sulfonamides Containing N-Acyl Moieties Catalyzed by Bismuth(III) Salts Under Both Solvent and Solvent-Free Conditions

Ferric Chloride-Mediated Transacylation of N-Acylsulfonamides

“…A general method for direct transacylation of typical N -acylsulfonamides is so far unavailable. , The transformation seemingly involves two stages, deacylation and acylation. Acylation of sulfonamides can be accomplished with a number of Lewis acids such as BiCl 3 , Bi­(OTf) 3 , CeCl 3 , SnCl 4 , ZnCl 2 , BF 3 ·Et 2 O, B­(C 6 F 5 ) 3 , TiCl 4 , , MoCl 5 , and Sc­(OTf) 3 in the presence of an acylating agent. Deacylation is usually performed by direct hydrolysis using hydrochloric acid and sulfuric acid .…”

“…From benzenesulfonamide (4a, 0.472 g, 3 mmol); white solid; yield: 0.600 g (87%); mp 99−101 °C (lit. 18 99−101 °C); R f = 0.25 (PE/EtOAc = 3:1). 1 H NMR (400 MHz, CDCl 3 ): δ 8.59 (br s, 1H), 8.08 (dd, J 1 = 8.5 Hz, J 2 = 1.3 Hz, 2H), 7.72−7.61 (m, 1H), 7.56 (t, J = 7.6 Hz, 2H), 2.24 (t, J = 7.4 Hz, 2H), 1.60 (h, J = 7.4 Hz, 2H), 0.87 (t, J = 7.4 Hz, 3H).…”

“…For the transacylation of amide 3ac performed in acetic anhydride, it was speculated that sequential coordination of anhydride carbonyl oxygen to the Lewis acidic center 54 followed by acylation of the amide nitrogen with the newly formed complex (18) gave an imide (19) concurrent with ferric acetate chloride anion (20), which then recombined and underwent deacylation to effect acyl exchange along with regeneration of the catalyst and a mixed carboxylic anhydride (AcOPiv). Hydrolysis of the mixed anhydride during workup provided two carboxylic acids, as supported by the formation of 1-naphthoic acid (7v′) during the transacetylation of Ntosyl-1-naphthamide (7v).…”

“…A number of methods have been developed for the synthesis of N -acylsulfonamides (Scheme A). Direct acylation of sulfonamides with an acylating agent such as carboxylic anhydride, , acid chloride, − carboxylic acid, , ester, or N -acylbenzotriazole is one of the most commonly employed protocols. N -acylsulfonamides can also be prepared through sulfonylation of amides with a sulfonyl chloride .…”

N-Monoacylation of Sulfonimidamides

“…To avoid the formation of N,N-diacylated sulfonamide byproducts, an acid-catalyzed reaction of carboxylic acid anhydrides or esters with amines is often applied. [14][15][16][17] As noted, we thought that the TBS-deprotected compound 2 could be diacylated to afford the undesired compound 4; therefore, the TBS-protected compound 1 was used in this work. Considering the undesired lability of 1 under acidic conditions, we focused on finding other acylating systems, using either benzoic acid or benzoyl chloride under basic conditions (Scheme 2).…”