Azetidines

Azetidines
Azetidines (general formula)
Azetidine
( S ) -azetidine-2-carboxylic acid (amino acid)

Azetidines are heterocyclic organic chemical substances that contain a four-membered ring consisting of one nitrogen atom and three carbon atoms. The group of substances derived from the azetidines of the azetidin-2-ones (β-lactams), penicillins and cephalosporins, which are used as medicinal substances ( antibiotics ), are of particular importance . ( S ) -Azetidine-2-carboxylic acid is a non-proteinogenic amino acid that occurs in lily of the valley ( Convallaria majalis ) and in small quantities in sugar beet, i.e. it is a natural product.

Manufacturing

Azetidine can be obtained from the thermal reaction of 1,3-diaminopropane with hydrochloric acid .

N -alkylated 3-hydroxyazetidines can be obtained by reacting the corresponding primary amines with epichlorohydrin at about 0.degree . C. and then heating to about 70.degree . If secondary amines are used, quaternary di- N -substituted 3-hydroxyazetidines are obtained.

Web links

Commons : Azetidines  - Collection of images, videos and audio files

Individual evidence

1. ↑ A. Ladenburg , J. Sieber: About trimethyleneimine and a new synthesis of β-picolines . In: Reports of the German Chemical Society . tape 23 , no. 2 , 1890, p. 2727-2731 , doi : 10.1002 / cber.189002302174 .
2. ↑ Robert H. Higgins, Quentin L. Eaton, Leroy Worth Jr., Myra V. Peterson: Preparation of 3-azetidinols with non-bulky 1-alkyl substituents . In: Journal of Heterocyclic Chemistry . tape 24 , no. 1 , 1987, pp. 255-259 , doi : 10.1002 / jhet.5570240149 .