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Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118
Graphical Abstract
Figure 1: Structure of naturally occurring and synthetic 2-pyrrolidone derivatives.
Figure 2: Structure of natural compounds containing a 1,5-dihydro-2H-pyrrol-2-one subunit.
Scheme 1: Synthesis of substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones 4 via three-component reaction.
Scheme 2: Proposed mechanistic path for the synthesis of substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones.
Scheme 3: Tautomerism of compounds 4a–c in DMSO.
Figure 3: View of the molecular structure of compound 10aa with atom labeling. Displacement ellipsoids are dr...
Figure 4: The PES of reaction for the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-dione 10ab enamine de...
Scheme 4: Reaction pathways from 4a, 4a’ to 10ab via IS5 in the gase phase.
Scheme 5: Reaction pathways from 4a to 10ab-v2 via IS3 in the gase phase.
Figure 5: The PES for the possible pathways (1), (2), (3), and (4) in ethanol solvent.
Figure 6: The optimized structures of some reactants, intermediates, transition states, and products in the p...
Beilstein J. Org. Chem. 2018, 14, 2190–2197, doi:10.3762/bjoc.14.192
Scheme 1: Macrocyclization towards homothiacalixarenes 3a and 3b [12].
Scheme 2: Cyclocondensation reaction of 4 and 5 towards [2 + 2] and [3 + 3] adducts.
Figure 1: X-ray crystal structure of alternate-linked-meta-para-thiacyclophane 6: (a) ball-and-stick represen...
Scheme 3: Proposed reaction mechanism towards alternate-linked-meta-para-thiacyclophanes.
Scheme 4: Attempted cyclocondensation with anisole derivative 13, products 14 and 15 were not formed.
Scheme 5: Macrocyclization under acidic conditions, with only traces of 6 and 7 observed.
Scheme 6: Post-functionalization of thiacyclophanes 6 and 7 with ethyl bromoacetate (17).
Scheme 7: Modification of the functionalized [2 + 2] adduct 18 towards an amide derivative 20 and acid deriva...
Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49
Figure 1: Triazolobenzodiazepine drugs.
Scheme 1: Retrosynthetic analysis towards 2,5-diketopiperazine fused triazolobenzodiazepine.
Scheme 2: Ugi 4-CR reaction.
Scheme 3: Synthesis of diketopiperazine-fused triazolobenzodiazepine 7a.
Figure 2: Generality in the synthesis of diketopiperazine-fused triazolobenzodiazepine 7. Reaction conditions...
Scheme 4: ‘One-pot’ synthesis of diketopiperazine-fused triazolobenzodiazepines 7a and 7b.
Scheme 5: Synthesis of hydantoin-fused triazolobenzodiazepine 10. Reaction conditions: 1. 2-azidobenzaldehyde ...
Figure 3: X-ray crystal structure of hydantoin-fused triazolobenzodiazepine 10a. (Displacement ellipsoids are...
Scheme 6: Mechanism of formation of diketopiperazine and hydantoin-fused triazolobenzodiazepines.