TiCl4-promoted direct N-acylation of sulfonamide with carboxylic ester

Fu, Shaomin; Lian, Xiaoyan; Ma, Tongmei; Chen, Wenhua; Zheng, Meifang; Zeng, Wei

doi:10.1016/j.tetlet.2010.08.092

Cited by 35 publications

(12 citation statements)

References 21 publications

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“…[14][15][16] This synthetic route generally works well, affording desired acylated products in satisfactory yields. [18] This methodology was further applied to a wider panel of esters, allowing the synthesis of N-acylsulfonamides of pharmaceutical interest. [17] Some reports from the literature describe the use of esters as acylating agents of sulfonamides, in the presence of Lewis acids.…”

Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

“…X-ray structure analysis revealed a different binding mode of 17 in LBD, accounting for the partial agonism. Recent studies showed for F I G U R E 1 0 N-acylsulfonamides targeting PPARs: PPARγ agonists (16,17) and PPARα antagonists (18,19) 19 antiproliferative effects in glioblastoma, pancreatic, and colorectal cancer models. In a similar way, fibrate-based N-acylsulfonamides were found PPARα antagonists, especially derivatives more hindered in the sulfonimidic portion.…”

Section: Ppar Agonists and Antagonistsmentioning

confidence: 99%

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N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

et al. 2017

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Sulfonamide is a common structural motif in naturally occurring and synthetic medicinal compounds. The rising interest in sulfonamides and N-acyl derivatives is attested by the large number of drugs and lead compounds identified in last years, explored in different fields of medicinal chemistry and showing biological activity. Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to N-acylsulfonamides, this review explores compounds of pharmaceutical interest, developed as enzymatic inhibitors or targeting receptors.

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Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

Section: Ppar Agonists and Antagonistsmentioning

confidence: 99%

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

et al. 2017

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“…Recently, we found that TiCl 4 could efficiently enhance the direct N-acylation of sulfonamide using carboxylic esters as acylating agents, and further studies on the reaction mechanism indicated that carboxylic esters were first transformed to their corresponding acids via O-alkyl cleavage and then condensed with sulfonamide to form N-acylated sulfonamide. [14] Therefore, we present an alternative ester cleavage method using Lewis acids as promoters under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

Lian

et al. 2011

Applied Organom Chemis

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A reliable and practical procedure for FeCl 3 -promoted ester cleavage has been developed. Lewis acids including TiCl 4 , ZnO and FeCl 3 etc. were investigated as promoters for O-alkyl cleavage of carboxylic acid ester. Under optimal reaction conditions, FeCl 3 (1.5 equiv.) was found to possess the highest activity and efficiently enhanced dealkylation of aryl esters, alkyl esters and aromatic heterocyclic esters to give their corresponding carboxylic acids in 54-98% yield, the method provides a complementary access to dealkylation of ester under neutral condition.

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“…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).…”

Section: Syn Thesismentioning

confidence: 99%

N-Monoacylation of Sulfonimidamides

Chen

2016

Synthesis

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N-Monoacylated sulfonimidamides, the aza analogue of Nacylsulfonamides which are a common motif in drug discovery, were exclusively synthesized by using a 1:1-premixed mixture of an acyl chloride and pyridazine as the acylating agent, while diacylation exclusively occurred when N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (EDC) was used as the coupling agent. The monoacylation is fast, easy to operate, and applicable to both aromatic and aliphatic acyl chlorides to give the corresponding products in moderate or high overall yields. A two-step N,N′-diacylated product exemplifies that the sulfonimidamide moiety provides one more handle than its sulfonamide isostere. This stepwise functionalization approach can be used to fine-tune the desired properties of compounds in medicinal chemistry.

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TiCl4-promoted direct N-acylation of sulfonamide with carboxylic ester

Cited by 35 publications

References 21 publications

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

N-Monoacylation of Sulfonimidamides

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TiCl4-promoted direct N-acylation of sulfonamide with carboxylic ester

Cited by 35 publications

References 21 publications

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

An efficient FeCl3‐promoted O‐alkyl cleavage of esters to carboxylic acids

N-Monoacylation of Sulfonimidamides

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An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids