A novel approach for the synthesis of alkyl and aryl sulfonamides

Shaabani, Ahmad; Soleimani, Ebrahim; Rezayan, Ali Hossein

doi:10.1016/j.tetlet.2007.01.091

Cited by 65 publications

(34 citation statements)

References 20 publications

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“…The crude product was purified by column chromatography with a mixture of petroleum ether and ethyl acetate (100:0 to 5:1) as eluent to give 62 (209 mg, 80 %) as a colourless solid. 1 [27] …”

Section: Methodsmentioning

confidence: 99%

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Gellert

Kahlcke

Feurer

et al. 2011

Chemistry A European J

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Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol%) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.

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Section: Methodsmentioning

confidence: 99%

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Gellert

Kahlcke

Feurer

et al. 2011

Chemistry A European J

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“…Synthesis of sulfonamides involves the nucleophilic attack of ammonia or amine on a sulfonyl halide (Chan et al, 2002;Shaabani et al, 2007). On the other hand, arylsulfonyl azides can be reduced to convert into arylsulfonamides (Boruah et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

2-Phenitidine derivatives as suitable inhibitors of butyrylcholinesterase

Abbasi

Aziz-Ur-Rehman

Qureshi

et al. 2013

Braz. J. Pharm. Sci.

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This manuscript reports the synthesis of a series of N-substituted derivatives of 2-phenitidine. First, the reaction of 2-phenitidine (1) with benzene sulfonyl chloride (2) yielded N-(2-ethoxyphenyl) benzenesulfonamide (3), which further on treatment with sodium hydride and alkyl halides (4a-g) furnished into new sulfonamides (5a-g). Second, the phenitidine reacted with benzoyl chloride (6) and acetyl chloride (8) to yield the reported N-benzoyl phenitidine (7) and N-acetyl phenitidine (9), respectively. These derivatives were characterized by infrared spectroscopy, ¹H-NMR, and EI-MS, and then screened against acetylcholinesterase, butylcholinesterase, and lipoxygenase enzyme, and were found to be potent inhibitors of butyrylcholinesterase alone.

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“…Although many efforts have been made towards the preparation of novel sulfonamides,11–20 the conventional synthesis involves the reaction of amino compounds with sulfonyl chlorides in the presence of a base or catalyst 21–25. Alternatively sulfonamides can be obtained by reacting sulfinic acid salts with an electrophilic nitrogen source such as hydroxylamine‐ O ‐sulfonic acid,26 or bis(2, 2, 2‐trichloroethyl) azodicarboxylate,27 by reacting sulfonic acid with isocyanides 28. Also recently, Deng and Mani reported the synthesis of sulfonamides by reaction of amines with sulfonyl chloride in water 29.…”

Section: Introductionmentioning

confidence: 99%

Convenient synthesis of sulfonamides from amines and p‐toluene sulfonyl chloride mediated by crosslinked poly(4‐vinylpyridine)

Zarchi

Aslani

2011

J of Applied Polymer Sci

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A general, mild, and convenient method has been developed for the synthesis of various N-substituted and N, N-disubstituted sulfonamides, as a class of sulfa drugs, from the corresponding amines and p-toluene sulfonyl chloride in the presence of readily available crosslinked poly-(4-vinylpyridine) as a catalyst, base or polymeric substrates. The use of polymeric catalyst simplifies routine sulfonylation of amines because it eliminates the traditional purification. The polymer can be removed quantitatively and it can be regenerated and reused for several cycles without losing its activity. EXPERIMENTAL ChemicalPoly(4-vinylpyridine) crosslinked with 2% divinyl benzene (100-200 mesh), [P 4 -VP], was purchased Correspondence to: M. A. Karimi Zarchi (makarimi@ yazduni.ac.ir).

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A novel approach for the synthesis of alkyl and aryl sulfonamides

Cited by 65 publications

References 20 publications

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

Triflic Acid Catalyzed Reductive Coupling Reactions of Carbonyl Compounds with O‐, S‐, and N‐Nucleophiles

2-Phenitidine derivatives as suitable inhibitors of butyrylcholinesterase

Convenient synthesis of sulfonamides from amines and p‐toluene sulfonyl chloride mediated by crosslinked poly(4‐vinylpyridine)

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