Harman Patil

Lactam

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Lactam Betalactam Wikipedia

lactams mechanisms of action and resistance


A lactam is a cyclic amide. The term is a portmanteau of the words lactone + amide.

Contents

Beta lactam antibiotics carboxylic acids and derivatives organic chemistry khan academy


Nomenclature

Greek prefixes in alphabetical order indicate ring size:

  • α-Lactam (3 ring atoms)
  • β-Lactam (4 ring atoms)
  • γ-Lactam (5 ring atoms)
  • δ-Lactam (6 ring atoms)
  • ε-Lactam (7 ring atoms)

  • Lactam Lactam Wikipedia

    This ring-size nomenclature stems from the fact that a hydrolyzed α-Lactam leads to an α-amino acid and a β-Lactam to a β-amino acid, etc.

    Synthesis

    General synthetic methods exist for the organic synthesis of lactams.

    Lactam Beta Lactam Antibiotics
  • Lactams form by the acid-catalyzed rearrangement of oximes in the Beckmann rearrangement.
  • Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction.
  • Lactams form from cyclisation of amino acids.
  • Lactams form from intramolecular attack of linear acyl derivatives from the nucleophilic abstraction reaction.
  • In iodolactamization an iminium ion reacts with an halonium ion formed in situ by reaction of an alkene with iodine.
  • Lactam Beta Lactam Antibiotics
  • Lactams form by copper-catalyzed 1,3-dipolar cycloaddition of alkynes and nitrones in the Kinugasa reaction
  • Diels-Alder reaction between cyclopentadiene and chlorosulfonyl isocyanate (CSI) can be utilized to obtain both β- as well as γ-lactam. At lower temp (−78°C), β-lactam is the preferred product. At optimum temperatures, a highly useful γ-lactam known as Vince Lactam is obtained.
  • Tautomerization to Lactim

    Lactam encitizendiumorgimagesthumb77fLactamsjpg2

    Lactim is a cyclic carboximidic acid compound characterized by an endocyclic carbon-nitrogen double bond. It is formed when lactam undergoes tautomerization.

    Reactions

  • Lactams can polymerize to polyamides.

  • Lactam Lactam Wikipedia
    Lactam Lactam Wikipedia

    References

    Lactam Wikipedia


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