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Beilstein J. Org. Chem. 2019, 15, 2069–2075, doi:10.3762/bjoc.15.204
Graphical Abstract
Figure 1: Structures of lilolidine, tivantinib and tarazepide.
Scheme 1: Access to α- and β-arylated lilolidine derivatives.
Scheme 2: Synthesis of α-arylated lilolidine derivatives.
Scheme 3: Synthesis of α,β-di(hetero)arylated lilolidine derivatives.
Scheme 4: Synthesis of α,β-diarylated lilolidine derivatives via successive direct arylations.
Scheme 5: Synthesis of 5,6-dihydrodibenzo[a,c]pyrido[3,2,1-jk]carbazoles via successive direct arylations.
Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208
Figure 1: Representative examples of bioactive imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, imidazopyr...
Scheme 1: Retrosynthetic scheme for the preparation of our target molecules A.
Scheme 2: Synthesis of enones 6 with a gem-difluoroalkyl side chain.
Scheme 3: Synthesis of 7a.
Figure 2: Structures of 7a and 7e by X-ray crystallography analysis.
Scheme 4: One-pot synthesis of 7a.
Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160
Figure 1: Substrates involved in deproto-metallation reaction.
Figure 2: ORTEP diagram (30% probability) of 2e.
Scheme 1: Synthesis of the azole substrates 1f and 2f.
Scheme 2: Deproto-metallation of 1c followed by iodolysis [33].
Scheme 3: Deproto-metallation of 1a and 2a followed by iodolysis.
Scheme 4: Deproto-metallation of 1b and 2b followed by iodolysis.
Scheme 5: Deproto-metallation of 1c and 2c followed by iodolysis.
Figure 3: ORTEP diagrams (30% probability) of 4c, 3d and 3e.
Scheme 6: Deproto-metallation of 1d and 2d followed by iodolysis.
Scheme 7: Deproto-metallation of 1e and 2e followed by iodolysis.
Scheme 8: N-arylation of the iodides 3b, 3d and 4d.
Figure 4: ORTEP diagram (30% probability) of 5d.
Figure 5: Calculated values of pKa(THF) of the compounds 1 and 2, and bromobenzene.
Figure 6: Antiproliferative activity (growth inhibition) of the tested compounds 1a,b,e,f, 2a,b and 5d at con...
Figure 7: Iodides previously formed as major products from the corresponding N-(4-methoxyphenyl)azoles using ...