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Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54
Graphical Abstract
Figure 1: The structures of chloroquine, hydroxychloroquine, and amodiaquine.
Scheme 1: Synthesis of 3-azolylpyrazoles 3a–c.
Scheme 2: Assumed mechanism for the formation of 1H-pyrazoles 3a–c.
Scheme 3: Synthesis of 3-aminopyrazoles 5b–k and 5-aminopyrazoles 5a and 5l–o.
Scheme 4: Orientation of nucleophilic attack of 7-chloro-4-hydrazinylquinoline on nitrobutadienes 4.
Scheme 5: Synthesis of oxazolidine 6 and pyrazole 7.
Scheme 6: A plausible mechanism for the formation of pyrazole 7.
Scheme 7: Synthesis of pyrazoles 9 and sulfoxide 10d.
Scheme 8: Synthesis of pyrazole 11.
Beilstein J. Org. Chem. 2014, 10, 1638–1644, doi:10.3762/bjoc.10.170
Scheme 1: SNVin reactions of pentachloro-2-nitro-1,3-butadiene (1).
Scheme 2: Formation of thiazolidin-4-ones 7–19.
Figure 1: Hindered rotation in the case of ortho- or meta-substituted aniline precursors.
Figure 2: X-ray analysis of thiazolidin-4-one 11.
Scheme 3: Assumed mechanism for the formation of thiazolidin-4-ones 7–18.
Scheme 4: Substitution reactions of the precursors 3 and 5 with additional amines.
Scheme 5: Synthesis of 5-arylmethylidenethiazolidin-4-ones 22–26 and 1H-pyrazoles 27, 28.
Scheme 6: Assumed mechanism for the formation of 1H-pyrazole 27.
Scheme 7: Formation of ethyl propanoate 29 and subsequent reactions.
Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69
Figure 1: Promising starting materials for biologically active compounds.
Figure 2: Pharmaceuticals bearing an azabicyclo[3.1.0]hexane unit.
Scheme 1: Synthesis of the azabicyclic hydrazone 6.
Scheme 2: Novel imidacloprid analogues 11, 12.
Figure 3: Stabilizing hydrogen bond in nitrobutadiene-derived imidacloprid analogues 9–12.
Scheme 3: Synthesis of the 4,4-bis(aminoazabicyclo[3.1.0]hexyl)-1-chloro-1,3-dinitrobutadiene 13.
Scheme 4: Synthesis of the highly substituted trisaminodichloronitrobutadiene 16.
Figure 4: Conceivable tautomeric structures of 16.
Scheme 5: Syntheses of the perfunctionalized isothiazole derivatives 20, 21.
Scheme 6: Preparation of the pyrazoles 27, 28, the pyrimidine 26 and the pyridopyrimidine 24.
Scheme 7: Proposed reaction mechanism for the formation of 27, 28.
Scheme 8: Attempted deprotection of the azabicyclic compounds 21,12, and 28.