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Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178
Graphical Abstract
Figure 1: Examples of biologically active oxazole and aminothiazole scaffolds.
Scheme 1: Strategies for the synthesis of 2,4,5-trisubstituted oxazole from azirine. a) I2, PPh3; b) NaH, 1H-...
Scheme 2: Scope of the α-azidochalcones. The reactions were carried out at reflux temperature, using 1 (1 mmo...
Scheme 3: Large-scale synthesis of 3i.
Figure 2: Large-scale synthesis of 3i. a) At the start of the reaction, b) after the reaction.
Scheme 4: Acetyl derivative of 3d.
Figure 3: ORTEP diagram of compound 5.
Scheme 5: Synthesis of S-methyl/benzylated products 6 and 7.
Scheme 6: Control experiments.
Scheme 7: Plausible mechanism proposed for the formation of 2,4,5-trisubstituted oxazoles 3.
Scheme 8: Reaction of vinyl azide 1 and 3 with ferric nitrate. Reactions were carried out at reflux temperatu...
Figure 4: X-ray crystal structure of 4h.
Beilstein J. Org. Chem. 2015, 11, 2021–2028, doi:10.3762/bjoc.11.219
Figure 1: Formation of substituted aziridine.
Figure 2: Various strategies for the formation of 2H-azirine.
Scheme 1: Attempted reaction for the synthesis of 3a.
Figure 3: Synthesis of α-amido-1,3-diketone (3a–o). Reaction conditions: α-azidochalcone 1 (1.0 equiv) and ca...
Scheme 2: Plausible mechanism.
Scheme 3: Attempted reaction with acid derivatives.
Scheme 4: Oxazole formation from 3.
Figure 4: Possible isomers for 7.
Scheme 5: Oxazole formation.
Figure 5: Synthesis of highly substituted 2-(trifluoromethyl)oxazoles (8a–e). Reaction conditions: α-azidocha...
Scheme 6: Mechanism for the formation of 8.
Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185
Figure 1: Selected examples of biologically active 2-aminothiophene derivatives.
Scheme 1: Some strategies for the synthesis of 2-aryl/alkylaminothiophenes and 3-nitrothiophenes.
Scheme 2: Our plan for the synthesis of N-substituted 3-nitrothiophen-2-amines.
Scheme 3: Synthesis of N-substituted 3-nitrothiophen-2-amines.
Figure 2: X-ray diffraction study of compound 3p.
Scheme 4: Proposed reaction sequence leading to the formation of 3.