A novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics.
beta-amino acids have been employed in the past as bifunctional building blocks in intramolecular Ugi multicomponent reactions to yield beta-lactam derivatives. By using 7-azabicyclo[2.2.1]heptane-2-carboxylic acid, a different outcome has been observed and rationalised. The final compounds are polyfunctionalised azabicyclic peptidomimetics, and further elaboration can be achieved exploiting an additional carboxylic group that is not involved in the multicomponent step.
Basso
Andrea
A
Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146 Genova, Italy. andreab@chimica.unige.it
Banfi
Luca
L
Guanti
Giuseppe
G
Riva
Renata
R
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D018716:Molecular Mimicry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry
C525410:7-azabicyclo(2.2.1)heptane; D000596:Amino Acids; D053961:Azabicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D047090:beta-Lactams