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Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence

Author:
Alcaide, Benito, Almendros, Pedro, Aragoncillo, Cristina, Callejo, Ricardo, Ruiz, M. Pilar, Torres, M. Rosario
Source:
Journal of organic chemistry 2012 v.77 no.16 pp. 6917-6928
ISSN:
1520-6904
Subject:
carboxylic acids, chemical reactions, chemical structure, diastereoselective synthesis, diastereoselectivity, organic chemistry, phenols, regioselectivity
Abstract:
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 C₂ and C₃ symmetric β-lactam-triazole hybrids, respectively.
Agid:
5498988