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Beilstein J. Org. Chem. 2017, 13, 895–902, doi:10.3762/bjoc.13.90
Graphical Abstract
Scheme 1: Envisaged general approach for the synthesis of the title compounds.
Scheme 2: Synthesis of 4-iodopyrazoles of type 3.
Scheme 3: Lithium–halogen exchange and subsequent carboxylation with iodopyrazoles 3a–d.
Scheme 4: Attempted cross-coupling reactions with 4-halopyrazoles 5 and 3a.
Scheme 5: Negishi couplings with 4-iodopyrazoles 3a,b.
Scheme 6: Formation of pyrazoloquinolizin-6-ium iodide 12 upon reaction of 3a with (phenylethynyl)zinc bromid...
Scheme 7: Prototropic tautomerism of compound 1a.
Figure 1: 1H NMR (in italics), 13C NMR and 15N NMR (in bold) chemical shifts of compound 9a (in CDCl3).