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Beilstein J. Org. Chem. 2015, 11, 884–892, doi:10.3762/bjoc.11.99
Graphical Abstract
Figure 1: Tetrahydroquinoline alkaloids of Galipea officinalis.
Scheme 1: Enaminone-based synthesis of (S)-cuspareine.
Scheme 2: The approaches to 2-aroylmethylidene-1,2,3,4-tetrahydroquinolines 1.
Scheme 3: The retrosynthetic analysis of the starting substrates for C–N cross-coupling.
Scheme 4: The synthesis of methyl 3-phenylpropionates. Conditions: (a) piperidine, PhCOOH, toluene, reflux 4 ...
Scheme 5: The synthesis of the starting β-enaminones. Conditions: (a) H2SO4, 65 °C, 46 h; (b) 1. t-BuOK/THF, ...
Figure 2: Ligands for C–N cross-coupling used in this work.
Figure 3: Deprotection of the hydroxy group in 1c to give the Galipein precursor 1e.
Figure 4: ORTEP (50% probability level) view for compound 1a. For selected parameters see Supporting Information File 1.
Beilstein J. Org. Chem. 2013, 9, 1463–1471, doi:10.3762/bjoc.9.166
Scheme 1: Syntheses of 1-arylpyridazinium salts.
Scheme 2: Suggested transformation of the cyclic enaminones into the corresponding bicyclic pyridazinium salt...
Scheme 3: The synthesis of the starting β-enaminones.
Scheme 4: Synthesis of the bicyclic pyridazinium salts using different methods.
Scheme 5: Possible mechanism of the formation of the pyridazinium salts 5.
Scheme 6: An attempt at synthesis of 5n and possible explanation of the failure.
Figure 1: ORTEP view of the cation of compound 5f showing the thermal ellipsoids at 30% probability level. Bo...
Figure 2: ORTEP view of the cation of compound 5l showing the thermal ellipsoids at 30% probability level. Bo...