Lactam

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From left to right, general structures of a β-lactam, a γ-lactam, a δ-lactam, and an ε-lactam. The specific structures are β-propiolactam, γ-butyrolactam, δ-valerolactam, and ε-caprolactam.

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

Nomenclature[edit]

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)

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[edit]

General synthetic methods exist for the organic synthesis of lactams.

Iodolactamization reaction

Preparation of VL and beta lactam

Tautomerization to Lactim[edit]

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

Reactions[edit]

See also[edit]

References[edit]

  1. ^ Spencer Knapp, Frank S. Gibson Organic Syntheses, Coll. Vol. 9, p.516 (1998); Vol. 70, p.101 (1992) Online article
  2. ^ Singh, R.; Vince, R. Chem. Rev. 2012, 112 (8), pp 4642–4686."2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics"
  3. ^ Pham, P.-T.; Vince, R. Phosphorus, Sulphur and Silicon 2007, 779-791.