In organic chemistry, the sulfonamidefunctional group (also spelled sulphonamide) is an organosulfur group with the structureR−S(=O)2−NR2. It consists of a sulfonyl group (O=S=O) connected to an amine group (−NH2). Relatively speaking this group is unreactive. Because of the rigidity of the functional group, sulfonamides are typically crystalline; for this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group.[1]
The structure of the sulfonamide group
A sulfonamide (compound) is a chemical compound that contains this group. The general formula is R−SO2NR'R" or R−S(=O)2−NR'R", where each R is some organic group; for example, "methanesulfonamide" (where R = methane, R' = R" = hydrogen) is CH3SO2NH2. Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group (−OH) with an amine group.
In medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide. The first sulfonamide was discovered in Germany in 1932.[2]
Sulfonamides can be prepared in the laboratory in many ways. The classic approach entails the reaction of sulfonyl chlorides with an amine.
A base such as pyridine is typically added to absorb the HCl that is generated. Illustrative is the synthesis of sulfonylmethylamide.[3] A readily available sulfonyl chloride source is tosyl chloride.[4] The reaction of primary and secondary amines with benzenesulfonyl chloride is the basis of the Hinsberg reaction, a method for detecting primary and secondary amines.
Sultams
"Sultam" redirects here. Not to be confused with Sultan.
Sultams are cyclic sulfonamides. Bioactive sultams include the antiinflammatory ampiroxicam and the anticonvulsant sulthiame. Sultams are prepared analogously to other sulfonamides, allowing for the fact that sulfonic acids are deprotonated by amines. They are often prepared by one-pot oxidation of disulfides or thiols linked to amines.[5] An alternative synthesis of sultams involves initial preparation of a linear sulfonamide, followed by intramolecular C-C bond formation (i.e. cyclization), a strategy that was used in the synthesis of a sultam-based deep-blue emitter for organic electronics.[6]
The disulfonimides are of the type R−S(=O)2−N(H)−S(=O)2−R’ with two sulfonyl groups flanking an amine.[10] As with sulfinamides, this class of compounds is used as catalysts in enantioselective synthesis.[10][11][12]
^Levy, Stuart B. (2002). The antibiotic paradox : how the misuse of antibiotics destroys their curative powers (2 ed.). Cambridge, Massachusetts: Perseus Publ. p. 51. ISBN9780738204406.
^ abJames, Thomas; van Gemmeren, Manuel; List, Benjamin (2015). "Development and Applications of Disulfonimides in Enantioselective Organocatalysis". Chem. Rev. 115 (17): 9388–9409. doi:10.1021/acs.chemrev.5b00128. PMID 26147232.
^Treskow, M.; Neudörfl, J.; Giernoth, R. (2009). "BINBAM – A New Motif for Strong and Chiral Brønsted Acids". Eur. J. Org. Chem. 2009 (22): 3693–3697. doi:10.1002/ejoc.200900548.
^García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. (2009). "A Powerful Chiral Counteranion Motif for Asymmetric Catalysis". Angew. Chem. Int. Ed. 48 (24): 4363–4366. doi:10.1002/anie.200901768. PMID 19437518.
March 02, 2023
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For the medical use of chemicals within this group see Sulfonamide medicine Not to be confused with Sulfamide In organic chemistry the sulfonamide functional group also spelled sulphonamide is an organosulfur group with the structure R S O 2 NR2 It consists of a sulfonyl group O S O connected to an amine group NH2 Relatively speaking this group is unreactive Because of the rigidity of the functional group sulfonamides are typically crystalline for this reason the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point Many important drugs contain the sulfonamide group 1 The structure of the sulfonamide group A sulfonamide compound is a chemical compound that contains this group The general formula is R SO2NR R or R S O 2 NR R where each R is some organic group for example methanesulfonamide where R methane R R hydrogen is CH3SO2NH2 Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group OH with an amine group In medicine the term sulfonamide is sometimes used as a synonym for sulfa drug a derivative or variation of sulfanilamide The first sulfonamide was discovered in Germany in 1932 2 Contents 1 Synthesis 2 Sultams 3 Sulfinamides 4 Disulfonimides 5 See also 6 ReferencesSynthesis EditSulfonamides can be prepared in the laboratory in many ways The classic approach entails the reaction of sulfonyl chlorides with an amine R 1 SO 2 Cl R 2 R 3 NH R 1 SO 2 NR 2 R 3 HCl displaystyle ce R 1SO2Cl R 2R 3NH gt R 1SO2NR 2R 3 HCl A base such as pyridine is typically added to absorb the HCl that is generated Illustrative is the synthesis of sulfonylmethylamide 3 A readily available sulfonyl chloride source is tosyl chloride 4 The reaction of primary and secondary amines with benzenesulfonyl chloride is the basis of the Hinsberg reaction a method for detecting primary and secondary amines Sultams Edit Sultam redirects here Not to be confused with Sultan Sultams are cyclic sulfonamides Bioactive sultams include the antiinflammatory ampiroxicam and the anticonvulsant sulthiame Sultams are prepared analogously to other sulfonamides allowing for the fact that sulfonic acids are deprotonated by amines They are often prepared by one pot oxidation of disulfides or thiols linked to amines 5 An alternative synthesis of sultams involves initial preparation of a linear sulfonamide followed by intramolecular C C bond formation i e cyclization a strategy that was used in the synthesis of a sultam based deep blue emitter for organic electronics 6 Sulfonamide based compounds Saccharin a cyclic sulfonamide that was one of the first artificial sweeteners discovered Sulfanilamide a compound that foreshadowed the development of sulfa drugs Sulfamethoxazole is a widely used antibiotic Ampiroxicam is a sultam used as an antiinflammatory drug Hydrochlorothiazide is a drug that features both acyclic and cyclic sulfonamide groups Camphorsultam is a sultam used as a chiral auxiliary in organic synthesis Sulfinamides EditThe related sulfinamides R S O NHR are amides of sulfinic acids R S O OH see sulfinyl Chiral sulfinamides such as tert butanesulfinamide p toluenesulfinamide 7 8 and 2 4 6 trimethylbenzenesulfinamide 9 are relevant to asymmetric synthesis Disulfonimides EditBis trifluoromethanesulfonyl aniline is a source of the triflyl CF3SO 2 group The disulfonimides are of the type R S O 2 N H S O 2 R with two sulfonyl groups flanking an amine 10 As with sulfinamides this class of compounds is used as catalysts in enantioselective synthesis 10 11 12 See also EditSulfonamide medicine Sulfamic acid SulfamideReferences Edit Actor P Chow A W Dutko F J McKinlay M A Chemotherapeutics Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a06 173 a href Template Cite encyclopedia html title Template Cite encyclopedia cite encyclopedia a CS1 maint multiple names authors list link Levy Stuart B 2002 The antibiotic paradox how the misuse of antibiotics destroys their curative powers 2 ed Cambridge Massachusetts Perseus Publ p 51 ISBN 9780738204406 Organic Syntheses Coll Vol 4 p 943 1963 Vol 34 p 96 1954 Online Article Organic Syntheses Coll Vol 5 p 39 1973 Vol 48 p 8 1968 Online Article Rassadin V Grosheva D Tomashevskii A Sokolov V Methods of Sultam Synthesis Chemistry of Heterocyclic Compounds 2013 Vol 49 p39 65 27 doi 10 1007 s10593 013 1231 3 Virk Tarunpreet Singh Ilawe Niranjan V Zhang Guoxian Yu Craig P Wong Bryan M Chan Julian M W 2016 Sultam Based Hetero 5 helicene Synthesis Structure and Crystallization Induced Emission Enhancement ACS Omega 1 6 1336 1342 doi 10 1021 acsomega 6b00335 PMC 6640820 PMID 31457199 Organic Syntheses Coll Vol 10 p 47 2004 Vol 77 p 50 2000 Link Org Synth 2007 84 129 138 Link Org Synth 2006 83 131 140 Link a b James Thomas van Gemmeren Manuel List Benjamin 2015 Development and Applications of Disulfonimides in Enantioselective Organocatalysis Chem Rev 115 17 9388 9409 doi 10 1021 acs chemrev 5b00128 PMID 26147232 Treskow M Neudorfl J Giernoth R 2009 BINBAM A New Motif for Strong and Chiral Bronsted Acids Eur J Org Chem 2009 22 3693 3697 doi 10 1002 ejoc 200900548 Garcia Garcia P Lay F Garcia Garcia P Rabalakos C List B 2009 A Powerful Chiral Counteranion Motif for Asymmetric Catalysis Angew Chem Int Ed 48 24 4363 4366 doi 10 1002 anie 200901768 PMID 19437518 Retrieved from https en wikipedia org w index php title Sulfonamide amp oldid 1121620068, wikipedia, wiki, book, books, library,
