MULTICOMPONENT REACTION FOR THE SYNTHESIS OF BETA-LACTAMS

Ricardo Bossioa, Carlos F. Marcosb, Stefano Marcaccinia,. Roberto Pepinoa
a Dipartamento di Chimica Organica Ugo Schiff, Università di Firenze
b Departamento de Química Orgánica en Cáceres, Universidad de Extremadura
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beta-lactam ringSources of the different atoms in the molecule: amine blue, isonitrile green, aldehyde yellow, acid redback to CPK

The title beta-lactams were synthesized at the University of Florenze by Doctor Stefano Marcaccini's group. The synthetic scheme involved a two step reaction sequence an the use of commercially available starting materials. The key step consists in a four component Ugi Reaction between E-cinnalmaldehyde, chloroacetic acid, cyclohexyl isocyanide and anilines. The so obtained products were cyclized by treatment with KOH in methanol, under very mild conditions, to give the beta-lactams in a good yield.

In this way, four different, commercially available and unexpensive products were combined in a sequence of two experimentally very simple reactions, to get a quite complex structure, present in many natural and biologically active products.

For a detailed description of this reactions see: A Facile Synthesis of Beta-Lactams Based on Isocyanide Chemistry. Ricardo Bossio, Carlos F. Marcos, Stefano Marcaccini ann Roberto Pepino. Tetrahedron Lett. 1997, 38, 2519.