[N:1]1([CH:8]=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:10]=O.[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([C:20]#[CH:21])[CH:17]=[CH:18][CH:19]=1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:15]=[C:16]([C:20]#[C:21][CH2:10][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([CH:8]=[O:9])[CH2:2][CH2:3]2)[CH:17]=[CH:18][CH:19]=1A mixture of 1.28 g (10 mmol) of 1,4-diazepane-1-carbaldehyde and 0.33 g (11 mmol) of paraformaldehyde in 13 ml of dioxane is heated at 80° C. until a homogeneous solution is obtained. 1.70 g (10 mmol) of 3-trifluoromethylphenylacetylene in solution in 7 ml of dioxane and 1.81 g (10 mmol) of copper diacetate are added. The mixture is heated at 80° C. for 4 hours. It is cooled to ambient temperature and diluted with 75 ml of ethyl acetate. The organic phase is washed with 25 ml of 30% ammonia solution and with saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 98/2/0.2 then 96/4/0.4 and 94/6/0.6 mixture of dichloromethane, methanol and 30% ammonia, to give 2.67 g of product in the form of a yellow oil.
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