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For reviews dealing with Pd-catalyzed reactions on halopyridazines and halopyridazin-3(2H)-ones see: (a) Maes, B. U. W.; Tapolcsányi, P.; Meyers, C.; Mátyus, P. Curr. Org. Chem. 2006, 10, 377.
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For recent reviews dealing (partly) with halogen-magnesium exchange see: a
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For recent reviews dealing (partly) with halogen-magnesium exchange see: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302.
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The Chemistry of Organomagnesium Compounds, Parts 1-2: R-Mg
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The scope of the process is unfortunately usually limited to electron rich pyridazines avoiding competitive addition reactions. For the addition reaction of s-BuLi on pyridazines and pyridazin-3(2H)-ones see Dal Piaz, V, Capperucci, A. Synlett 1998, 762
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The scope of the process is unfortunately usually limited to electron rich pyridazines avoiding competitive addition reactions. For the addition reaction of s-BuLi on pyridazines and pyridazin-3(2H)-ones see Dal Piaz, V.; Capperucci, A. Synlett 1998, 762.
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A similar reaction involving the additional substitution of a C-4 halogen by a dimethylamino group was observed when using 3,6-dimethoxy-4,5-diodo- and 3,6-dimethoxy-4,5-dibromopyridazine as substrates, i-PrMgCl as halogen-magnesium exchange reagent and DMF as the electrophile: see ref 5f
-
A similar reaction involving the additional substitution of a C-4 halogen by a dimethylamino group was observed when using 3,6-dimethoxy-4,5-diodo- and 3,6-dimethoxy-4,5-dibromopyridazine as substrates, i-PrMgCl as halogen-magnesium exchange reagent and DMF as the electrophile: see ref 5f.
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0036262798
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For ipso substitutions in (η6-arene)tricarbonylchromium, see
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6-arene)tricarbonylchromium, see: Rose-Munch, F.; Rose, E. Eur. J. Inorg. Chem. 2002, 6, 1269.
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Rose-Munch, F.1
Rose, E.2
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39
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73149087114
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For regioselective bromine-magnesium exchange in dibromopyridines, see: Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349. For regioselective bromine-magnesium exchange in 4,5-dibromo-2,6-dimethoxypyrimidine see: Boudet, N.; Knochel, P. Org. Lett. 2006, 8, 3737.
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For regioselective bromine-magnesium exchange in dibromopyridines, see: Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349. For regioselective bromine-magnesium exchange in 4,5-dibromo-2,6-dimethoxypyrimidine see: Boudet, N.; Knochel, P. Org. Lett. 2006, 8, 3737.
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A Scifinder database search revealed that 70% of the molecules synthesized in this manuscript (with the specific substituents on C-4 and C-5 shown in the tables, schemes and figures, leaving the N-2 and C-6 substituents undefined) were hitherto unknown.
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A Scifinder database search revealed that 70% of the molecules synthesized in this manuscript (with the specific substituents on C-4 and C-5 shown in the tables, schemes and figures, leaving the N-2 and C-6 substituents undefined) were hitherto unknown.
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