[CH2:1]1[CH2:11][CH2:10][N:9]2[C:4](=[N:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.[CH:12]1[CH:16]=[C:15]([CH2:17][C:18]2[NH:22][CH:21]=[CH:20][CH:19]=2)[NH:14]C=1.[Mg+2].[Br-].[Br-].[CH2:26](Cl)Cl.[C:29]1(C)C=CC=C[CH:30]=1>>[C:2]12[CH:3]=[C:4]3[N:5]=[C:6]([CH:29]=[CH:30]3)[CH:7]=[C:8]3[NH:9][C:10]([CH:11]=[CH:1]3)=[CH:26][C:21]3=[N:22][C:18]([CH:19]=[CH:20]3)=[CH:17][C:15]([NH:14]1)=[CH:16][CH:12]=2Synthesis of Mg-1 via 1,9-Diformyldipyrromethane. By following the general procedure, a sample of DBU (0.750 mL, 5.00 mmol) was added dropwise to a suspension of 3 (36 mg, 0.25 mmol) and 4 (50 mg, 0.25 mmol) in toluene (5 mL). MgBr2 (276 mg, 1.5 mmol, 3.00 mol equiv) was added to the reaction mixture in a single portion. The reaction mixture was heated to 115° C. (preheated oil bath temperature 115° C.) with exposure to air for 36 h. Column chromatography (alumina, grade V, CH2Cl2) afforded Mg-1 in 18% yield.
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