[O:1]=[C:2]([CH2:7][C:8](=[O:10])[CH3:9])[CH2:3][CH2:4][C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Li+].C(Cl)(Cl)Cl.CO.O>S(=O)(=O)(O)O.CN(C)C=O.C(O)(=O)C.CO.C(Cl)Cl>[O:1]=[C:2]([CH2:7][C:8](=[O:10])[CH3:9])[CH2:3][CH2:4][C:5]1[NH:13][N:12]=[N:11][N:6]=1A mixture of the 3,5-dioxohexylcyanide (2.78 gm; 20 mmole), lithium azide (1.08 gm; 22 mmole) and sulfuric acid (one drop) in 10 ml dry dimethylformamide is heated to 100-120 degrees. Progress of the reaction may be checked by TLC (silica gel; chloroform:methanol 97:3). When no starting material remaines, the reaction is cooled and 20 ml of water added. The reaction is taken to dryness under reduced pressure and the residue fractionated by silica gel flash column chromatography using methylene chloride:glac. acetic acid:methanol 100:3:3 as eluant. Fractions containing the product may be pooled and concentrated.
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