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Sulfonamide

sulfonamides, sulfonamide experiments during the holocaust
In chemistry, the sulfonamide functional group also spelled sulphonamide is -S=O2-NH2, a sulfonyl group connected to an amine group Relatively speaking this group is unreactive The amine center is no longer basic The S-N bond is cleaved only with difficulty 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

A sulfonamide compound is a compound that contains this group The general formula is RSO2NH2, where R is some organic group For example, "methanesulfonamide" is CH3SO2NH2 Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group 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

Contents

  • 1 Synthesis
  • 2 Sultams
  • 3 Sulfinamides
  • 4 Disulfonimides
  • 5 See also
  • 6 References

Synthesis

Sulfonamides can be prepared in the laboratory in many ways The classic approach entails the reaction of sulfonyl chlorides with an amine

RSO2Cl + R2NH → RSO2NR2 + HCl

A base such as pyridine is typically added to absorb the HCl that is generated Illustrative is the synthesis of sulfonylmethylamide A readily available sulfonyl chloride source is tosyl chloride 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

Sultams are cyclic sulfonamides Bioactive sultams include the antiinflammatory ampiroxicam and the anticonvulsant sultiame 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 An alternative synthesis of sultams involves initial preparation of a linear sulfonamide, followed by intramolecular C-C bond formation ie cyclization, a strategy that was used in the synthesis of a sultam-based deep-blue emitter for organic electronics

Sulfinamides

The related sulfinamides RS=ONHR are amides of sulfinic acids RS=OOH see sulfinyl Chiral sulfinamides such as tert-butanesulfinamide, p-toluenesulfinamide and 2,4,6-trimethylbenzenesulfinamide are relevant to asymmetric synthesis

Disulfonimides

The related disulfonimides are of the type R-S=O2-NH-S=O2-R' with two sulfonyl groups flanking an amine As with sulfinamides this class of compounds is used as catalysts in enantioselective synthesis

See also

  • Sulfonamide medicine
  • Sulfamic acid
  • Sulfamide

References

  1. ^ Actor, P; Chow, A W; Dutko, F J; McKinlay, M A 2005, "Chemotherapeutics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:101002/14356007a06_173 CS1 maint: Multiple names: authors list link
  2. ^ Levy, Stuart B 2002 The antibiotic paradox : how the misuse of antibiotics destroys their curative powers 2 ed Cambridge, Mass: Perseus Publ p 51 ISBN 9780738204406 
  3. ^ Organic Syntheses, Coll Vol 4, p943 1963; Vol 34, p96 1954 Online Article
  4. ^ Organic Syntheses, Coll Vol 5, p39 1973; Vol 48, p8 1968 Online Article
  5. ^ Rassadin, V; Grosheva, D; Tomashevskii, A Sokolov, V "Methods of Sultam Synthesis" Chemistry of Heterocyclic Compounds 2013, Vol 49, p39-65 27 doi:101007/s10593-013-1231-3
  6. ^ Virk, Tarunpreet Singh; Ilawe, Niranjan V; Zhang, Guoxian; Yu, Craig P; Wong, Bryan M; Chan, Julian M W 2016 "Sultam-Based Heterohelicene: Synthesis, Structure, and Crystallization-Induced Emission Enhancement" ACS Omega 1: 1336–1342 doi:101021/acsomega6b00335 
  7. ^ Organic Syntheses, Coll Vol 10, p47 2004; Vol 77, p50 2000 Link
  8. ^ Org Synth 2007, 84, 129-138 Link
  9. ^ Org Synth 2006, 83, 131-140 Link
  10. ^ a b Development and Applications of Disulfonimides in Enantioselective Organocatalysis Thomas James, Manuel van Gemmeren, and Benjamin List Chem Rev, 2015 doi:101021/acschemrev5b00128
  11. ^ Treskow, M, Neudörfl, J and Giernoth, R 2009, BINBAM – A New Motif for Strong and Chiral Brønsted Acids Eur J Org Chem, 2009: 3693–3697 doi:101002/ejoc200900548
  12. ^ García-García, P, Lay, F, García-García, P, Rabalakos, C and List, B 2009, A Powerful Chiral Counteranion Motif for Asymmetric Catalysis Angew Chem Int Ed, 48: 4363–4366 doi:101002/anie200901768

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