A lactam (the noun is a portmanteau of the wods 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. This article or section does not cite its references or sources. ... A lactone is a cyclic ester in organic chemistry. ... Amide functional group In chemistry, an amide is one of two kinds of compounds: - the organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group (pictured to the right); or - a particular kind of nitrogen anion. ... Simple aromatic rings are aromatic organic compounds (also known as arenes or aromatics) that consist only of conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds. ... Amide functional group In chemistry, an amide is one of two kinds of compounds: - the organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group (pictured to the right); or - a particular kind of nitrogen anion. ... A beta-lactam (β-lactam) or penam is a lactam with a heteroatomic ring structure, consisting of three carbon atoms and one nitrogen atom. ... Beta (upper case Î’, lower case β) is the second letter of the Greek alphabet. ... Gamma (uppercase Γ, lowercase γ) is the third letter of the Greek alphabet. ... Look up Δ, δ in Wiktionary, the free dictionary. ... Because of technical limitations, some web browsers may not display some special characters in this article. ...

Synthesis

General synthetic methods exist for the organic synthesis of lactams. Organic synthesis is the construction of organic molecules via chemical processes. ...

• Lactams form by the acid-catalyzed rearrangement of oximes in the Beckmann rearrangement.
• Lactams form from cyclic ketones and ammonia in the Schmidt reaction.
• lactams form from cyclisation of amino acids.
• In iodolactamization ^[1] 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

In chemistry, the Beckmann rearrangement is the rearrangement of a ketoxime to the corresponding amide in concentrated sulfuric acid, phosphorus pentachloride or a few other catalysts. ... In chemistry, an amino acid is any molecule that contains both amino and carboxylic acid functional groups. ... An iminium salt or ion in organic chemistry has the general structure R1-CH=NH+-R2 and is as such a protonated imine. ... A halonium ion in organic chemistry is any onium ion containing a bridged halogen atom carrying a positive charge. ... The chemical structure of ethylene, the simplest alkene. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Atomic mass 126. ... Image File history File links Download high-resolution version (996x184, 4 KB) Iodolactamization of alkenes I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... A nitrone is the N-oxide of an imine and a functional group in organic chemistry. ...

Reactions

• Lactams can polymerize to polyamides.

A polyamide is a polymer containing monomers joined by peptide bonds. ...

See also

• β-lactam with a four-membered ring found in beta-lactam antibiotics. Penicillin, considered the most famous antibiotic, is a β-lactam antibiotic.
• Lactone, a cyclic ester.
• Caprolactam

A beta-lactam (β-lactam) or penam is a lactam with a heteroatomic ring structure, consisting of three carbon atoms and one nitrogen atom. ... β-lactam antibiotics are a broad class of antibiotics including penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ... Penicillin nucleus Penicillin (sometimes abbreviated PCN) refers to a group of β-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... A lactone is a cyclic ester in organic chemistry. ... General formula of a carboxylate ester. ... Caprolactam (C6H11ON) is the monomer used in the production of nylon 6. ...

References

1. ^ Spencer Knapp, Frank S. Gibson Organic Syntheses, Coll. Vol. 9, p.516 (1998); Vol. 70, p.101 (1992) Online article

Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...

External links

• Links to external chemical sources