Cl[C:2]1[C:3]([N+:21]([O-:23])=[O:22])=[C:4]([CH3:20])[C:5]2[NH:6][C:7](=[O:19])[C:8]3[CH:18]=[CH:17][CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[CH3:24][SeH-:25](C)=[Se].[BH4-].[Na+].N1C=CN=CC(=O)C=1.C(CN)O>C(O)(C)C.O1CCOCC1>[CH2:13]([N:10]1[C:9]2[N:15]=[CH:16][CH:17]=[CH:18][C:8]=2[C:7](=[O:19])[NH:6][C:5]2[C:4]([CH3:20])=[C:3]([N+:21]([O-:23])=[O:22])[C:2]([Se:25][CH3:24])=[N:12][C:11]1=2)[CH3:14]
To a mixture of 2-chloro-5,11-dihydro-11-ethyl-4-methyl-3-nitro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.063 g) and dimethyldiselenide (0.11 g) in isopropanol (0.5 mL) in a pressure tube was added sodium borohydride (0.006 g). The tube was sealed and heated at 110° C. for 5 minutes and then left at room temperature for 3 days. The mixture was eluted from a short silica gel column (chloroform) and then fractionated by preparative layer chromatography to give a mixture of 2-chloro-5,11-dihydro-11-ethyl-4-methyl-3-nitro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one and 5,11-dihydro-11-ethyl-4-methyl-2-methylseleno-3-nitro- 6H-dypyrido[3,2-b:2', 3'-e][1,4]diazepin-6-one. The mixture was dissolved in dioxan (1 mL) and ethanolamine (0.1 g) was added. The mixture was heated at 100° C. for 2 hours whereupon the remaining starting material had reacted. Evaporation of the solvent and chromatography over silica gel gave the title compound which crystallized on trituration with diisopropyl ether, m.p. 261°-267° C. dec.
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