A Facile and Eco-Friendly Method for the Synthesis of Sulfonamide and Sulfonate Carboxylic Acid Derivatives—X-ray Structure, Hirshfeld Analysis and Spectroscopic Characterizations (original) (raw)
Related papers
Rasayan journal of Chemistry, 2017
This current research describes the eco-friendly synthesis of N-(s-phenyl)-3-phenyl-2-(phenyl sulfonamido) propanamides which are sulfonamide bearing diversified carboxamide moieties. The incorporation of amido functionality into the sulfonamide moieties was herein achieved in three steps in a cost-effective manner by starting from cheap amino acid, phenyl alanine which was reacted with benzenesulfonyl chloride to produce sulfonamide which upon subsequent esterification followed by amidation furnished carboxamido-incorporated sulfonamide analogs 9a-j in good to excellent yield. The completion of reaction processes was authenticated with Thin Layer Chromatography (TLC) and the chemical structures were validated through the elemental analysis result as well as spectroscopic means which include FT-IR, UV, 1 H and 13 C NMR. The technique used herein was found to be efficient and cost-effective for the production of the series of carboxamide diversified sulfonamide derivatives.
ChemInform Abstract: Recent Advances in the Synthesis of Sulfonic Acids
ChemInform, 2002
This review article surveys recent achievements in the preparation and biological properties evaluation of fluorinated aminophosphonates and aminophosphonic acids. Recently, in view of various important biological applications of the fluorinated aminophosphonic acid derivatives, the development of suitable synthetic methodologies for their preparation in racemic and in optically pure form has been a topic of great interest. Considerable progress has been made in asymmetric synthesis of fluorinated acyclic aminophosphonates and aminophosphonic acids using catalytic enantioselective reduction of fluorinated a-iminophosphonates, catalytic enantioselective addition of alkyl phosphites to fluorinated imines, and diastereoselective addition of alkyl phosphites to chiral fluorinated imines. A new efficient access to CF 3substituted cyclic a-aminophosphonates has been developed based on metal-catalyzed carbene transfer reactions with diethyl 1-diazo-2,2,2-trifluoroethylphosphonate. New processes, e.g. enantioselective alkynylation and nucleophilic aromatic substitution involving fluorinated substrates are also considered.
Recent Advances in the Synthesis of Sulfonylureas
European Journal of Organic Chemistry, 2021
Sulfonylureas are employed in a variety of applications including use as drugs to treat type II diabetes and as plant growth regulators or herbicides. Traditionally, the synthesis of sulfonylureas has been accomplished either by the treatment of sulfamides with isocyanates in the presence of a base or through sulfonamides conversion into N-sulfonyl isocyanates or N-sulfonyl carbamate derivatives which provide the corresponding sulfonylureas upon treatment with amines. Both the approaches are severely limited by the weak nucleophilicity of sulfamides and by the difficulty in synthesizing and handling isocyanate species. Such a drawback could be mitigated by the emergence of protocols establishing the labile electrophilic functional groups in situ so that their coupling with nucleophilic partners takes place one-pot. Recently, the development of environmentally friendly methods to prepare sulfonylurea containing compounds without using harmful reagents has attracted considerable attention. The aim of the minireview is to explore the different protocols emerged in the literature to generate sulfonylureas giving importance to the reaction mechanisms of crucial synthetic steps.
Acta Chimica Slovenica, 2020
A series of new solid esters was synthesized by using greener chemistry strategy involving simple reaction of an alcohol with sulfonamide ligand. Characterization study of these methyl (1), ethyl (2) isopropyl (3) and n-butyl (4) ester of 4-((4-chlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid was done by using FTIR, NMR mass spectrometry and X-ray crystallography. The compounds were optimized with Gaussian software according to basis set B3LYP/6-31G(d,p) and their different parameters related to structure were calculated. Furthermore, all compounds of the series were screened for their in vitro biological applications involving anti-bacterial (Chromohalobactor salixgens, Halomonas halofila, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Shiegella sonnei), anti-fungal (Aspergillus niger), anti-oxidant (DPPH scavenging activity) and enzyme inhibition (acetylcholine esterase and butyrylcholine esterase) study. Sulfonamide based esters were also docked against selected enzymes (AChE and BChE) using MOE software for their mode of binding. Results obtained from these biological evaluations showed that such compounds have potential against targeted activity.
A novel approach for the synthesis of alkyl and aryl sulfonamides
Tetrahedron Letters, 2007
A novel approach for the synthesis of alkyl and aryl sulfonamides by the reaction of sulfonic acids, isocyanides and water in dichloromethane is reported at ambient temperature in excellent yields within 20 min. To the best of our knowledge this is the first report on the synthesis of this biologically important family using easily available sulfonic acids and isocyanides.
Tetrahedron Letters, 2007
The N-acylation of sulfonamides with carboxylic acid anhydrides in the presence of Lewis acids is described. Several Lewis acids such as BF 3 AEEt 2 O, ZnCl 2 , MoCl 5 , TiCl 4 , B(C 6 F 5 ) 3 , Sc(OTf) 3 and I 2 were found to catalyze the reaction efficiently to furnish the N-acylated products in good yields under solvent-free conditions. The reactions of various sulfonamides were studied with different carboxylic acid anhydrides including the less reactive benzoic and pivalic anhydrides, in the presence of 3 mol % ZnCl 2 as the catalyst. Carboxylic acids were also successfully used as acylating agents via the mixed anhydride method.