cyclic amides, nitrogen analogs of lactones
- Italian: lattame
Usage notesGreek prefixes indicate the ring size e.g. α- 3-membered, β- 4-membered.
A lactam (the noun is a portmanteau of the words lactone + amide) is a cyclic amide. Prefixes may indicate the ring size: β-lactam (4-membered), γ-lactam (5-membered), δ-lactam (6-membered ring). That order in the nomenclature is because beta β, gamma γ and delta δ are the second, third and fourth letters in the alphabetical order of the Greek alphabet, respectively.
SynthesisGeneral synthetic methods exist for the organic synthesis of lactams.
- 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.
- In iodolactamization an iminium ion reacts with an halonium ion formed in situ by reaction of an alkene with iodine.
- Lactams form by copper catalyzed 1,3-dipolar cycloaddition of alkynes and nitrones in the Kinugasa reaction
- Lactams can polymerize to polyamides.
lactam in German: Lactame
lactam in French: Lactame
lactam in Hebrew: לקטם
lactam in Malay (macrolanguage): Laktam
lactam in Japanese: ラクタム
lactam in Polish: Laktamy
lactam in Portuguese: Lactama
lactam in Finnish: Laktaami
lactam in Swedish: Laktam