Regio- and diastereoselective synthesis of β-lactam-triazole hybrids via Passerini/CuAAC sequence.
Passerini (P-3CR) and Passerini-Smiles reactions were investigated in azetidine-2,3-diones, affording the corresponding 3,3-disubstituted-β-lactams with complete diastereoselectivity in high yields. The study has been carried out using different isocyanides, carboxylic acids, and phenols showing the scope of both reactions. In addition, the regioselective synthesis of highly functionalized β-lactam-triazole hybrids has been developed via a Passerini/CuAAC sequence. Interestingly, the use of dialkynes/diazides or trialkynes/triazides as linkers in the CuAAC step has allowed the synthesis of C(2) and C(3) symmetric β-lactam-triazole hybrids, respectively.
Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Benito
B
Alcaide
Pedro
P
Almendros
Cristina
C
Aragoncillo
Ricardo
R
Callejo
M Pilar
MP
Ruiz
M Rosario
MR
Torres