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Beilstein J. Org. Chem. 2025, 21, 2202–2210, doi:10.3762/bjoc.21.167
Graphical Abstract
Figure 1: Some bioactive molecules bearing triazole, tetrazole, and 1,4-benzodiazepin rings.
Scheme 1: Ugi–azide reaction for the synthesis of 1,5-DS-T-containing heterocycles.
Scheme 2: Proposed Ugi–azide-initiated synthesis of polyheterocyclic scaffolds 7 and 8.
Scheme 3: 4-CR vs stepwise Ugi–azide reactions for the synthesis of 7a.
Scheme 4: Synthesis of benzodiazepines 7a–k. Reaction conditions: 1) 0.2 mmol each of 2-azidobenzaldehyde (1a...
Scheme 5: Synthesis of polycyclic compound 8a.
Scheme 6: Synthesis of product analogs 8. Reaction conditions: 1) 0.2 mmol each of 2-azidobenzaldehyde (1a) a...
Scheme 7: Control reactions to trap the Ugi–azide adduct.
Figure 2: 1H NMR spectra of compounds 6a (red) and 8a (blue).
Scheme 8: Gram-scale one-pot synthesis of 8a.