Sulfonamide

Source: Wikipedia, the free encyclopedia.
For the medical use of chemicals within this group, see Sulfonamide (medicine).
Not to be confused with Sulfamide.
The structure of the sulfonamide group

In

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]

A sulfonamide (compound) is 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]

Synthesis and reactions

Sulfonamides can be prepared in the laboratory in many ways. The classic approach entails the reaction of

sulfonyl chlorides with an amine
.

RSO2Cl + R'2NH → RSO2NR'2 + HCl

A base such as pyridine is typically added to absorb the HCl that is generated. Illustrative is the synthesis of sulfonylmethylamide.[3] 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.

Sulfonamides undergo a variety of acid-base reactions. The N-H bond can be deprotonated. The alkylsulfonamides can be deprotonated at carbon. Arylsulfonamides undergo

ortho-lithiation.[4]

Sultams

"Sultam" redirects here. Not to be confused with Sultan.

Sultams are cyclic sulfonamides. Bioactive sultams include the antiinflammatory

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]

Sulfinamides

The related

asymmetric synthesis
.

Disulfonimides

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.

enantioselective synthesis.[10][11][12]

See also

References

  1. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link
    )
  2. ISBN 9780738204406
    .
  3. doi:10.15227/orgsyn.034.0096
    .
  4. ISBN 978-0-470-03439-2
    .
  5. doi:10.1007/s10593-013-1231-3
    .
  6. PMID 31457199
    .
  7. ^ Organic Syntheses, Coll. Vol. 10, p.47 (2004); Vol. 77, p.50 (2000). Link
  8. ^ Org. Synth. 2007, 84, 129-138 Link
  9. ^ Org. Synth. 2006, 83, 131-140 Link
  10. ^
    PMID 26147232
    .
  11. doi:10.1002/ejoc.200900548
    .
  12. PMID 19437518
    .
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