144150-84-5

Upstream product

• 52533-88-7 5-bromo-N-tosylpentanamide 
• 70-55-3 toluene-4-sulfonamide 
• 638-29-9 n-valeryl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 109-52-4 valeric acid 
• 110-62-3 pentanal 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 2082-59-9 pentanoic anhydride 

Downstream Products

• 144150-85-6 N-methyl-N-tosylvarleramide 
• 626-97-1 pentamide 
• 536-57-2 p-toluene sulfinic acid 

Relevant academic research and scientific papers

Synthesis, characterization, and antimicrobial evaluation of sulfonamides containing N-acyl moieties catalyzed by bismuth(III) salts under both solvent and solvent-free conditions

Efficient N-acylation of sulfonamides with both readily available carboxylic acid chlorides and anhydrides has been carried out with catalysis by bismuth(III) salts including BiCl3 and Bi (OTf)3. The reactions proceed rapidly in both heterogeneous and solvent-free conditions and afforded the corresponding N-acylsulfonamides in good to excellent yields. The mild reaction conditions and low toxicity of bismuth salts make this procedure attractive and in close agreement with the goals of green chemistry. Some of the synthesized compounds were evaluated in vitro as antimicrobial agents against representative strains of Gram-positive (Staphylococcus aureus ATCC 25922, clinical strains of Staphylococcus aureus VISA and Enterococcus spp.) and Gram-negative bacteria (Pseudomonas aeruginosa ATCC 27853, clinical strains of Klebsiella pneumonia and Escherichia coli) and as antifungal agents against Candida albicans (clinically isolated) by both disc diffusion and minimal inhibition concentration (MIC) methods. All these bacteria and fungi studied were screened against some antibiotics to compare with our chemicals' zone diameters.

Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds

An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.

Iodide as an activating agent for acid chlorides in acylation reactions

Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

Iron-catalyzed nitrene insertion reaction for facile construction of amide compounds

A facile method for the construction of amide compounds from aldehydes by an iron-catalyzed nitrene insertion reaction has been developed. Both aryl and aliphatic aldehydes can directly afford the corresponding amides with an iron(II)-terpyridine (tpy) complex formed in situ as catalyst, and PhI=NTs as nitrogen source under mild reaction conditions. An ESI-MS study revealed the formation of [Fe(tpy)NTs)]+ as a reaction intermediate. Georg Thieme Verlag Stuttgart - New York.

A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts

Some metal hydrogen sulfates were used as acid catalysts in the N-acylation of different sulfonamides using carboxylic acid chlorides and anhydrides as acylating agents under both heterogeneous and solvent-free conditions. Al(HSO4)3

Synthesis, in vitro antibacterial and carbonic anhydrase II inhibitory activities of N-acylsulfonamides using silica sulfuric acid as an efficient catalyst under both solvent-free and heterogeneous conditions

Silica sulfuric acid catalyzes efficiently the reaction of sulfonamides with both carboxylic acid anhydrides and chlorides under solvent-free and heterogeneous conditions. All the reactions were done at room temperature and the N-acylsulfonamides were obtained with high yields and purity via an easy work-up procedure. This method is attractive and is in a close agreement with green chemistry. These compounds were also investigated for antibacterial activity, including Gram-positive cocci and Gram-negative bacilli, and carbonic anhydrase II inhibitory activity.

ELECTROCHEMICAL STUDIES ON HALOAMIDES. PART IX. ω-BROMO-N-TOSYLALKANAMIDES

The electrochemical behaviour of ω-bromo-N-tosylalkanamides 1a-d at a mercury cathode in N,N-dimethylformamide solutions containing tatraethylammonium perchlorate as supporting electrode has been investigated.The cleavage of the N-S bond turns out to be selective for bromotosylvaleramide 1a and butyramide 1b giving high yields of the corresponding N-unsubstituted lactams, 2-piperidone 6a and 2-pyrrolidone 6b, irrespective of the reaction conditions.It is suggested that ring closure occurs via intramolecular nucleophilic substitution of nitrogen anions formed by dissociative electron transfer from the electrode or acid-base reaction in the bulk of the solution.Bromotosylpropanamide 1c undergoes unselective breaking of both electroactive groups C-Br and N-S and a mixture of products arising from their cleavage is formed.By way of contrast, bromotosylacetamide 1d undergoes selective cleavage of the C-Br bond giving, inter alia, its conjugate base whose stebility allowed us to further clarify the effect of added acids and bases on its voltammetric behaviour.