Hydrogenation of benzodiazepinones
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 6, June, 2017
1061
were 17.4 and 19.3 min, respectively, and the retention time
of 4-phenyl-1,3-dihydro-2H-1,5-benzodiazepine-2-one (1a)
was 9.1 min. The retention times for the enantiomers of
4-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepinone-2-one
(–)-2b and (+)-2b were 16.5 and 23.4 min, respectively, and
the retention time of 4-methyl-1,3-dihydro-2H-1,5-benzodi-
azepine-2-one (1b) was 6.6 min. Conversions of 1a and 1b
were determined by 1H NMR spectroscopy; the spectral
characteristics of products 2a and 2b correspond to the ear-
lier published data.10 4-Phenyl-1,3-dihydro-2H-1,5-benzodiaze-
pine-2-one (1a),11 (Sa)-2-(piperidin-1-yl)-dinaphtho[2,1-d:1´,2´-f]
[1,3,2]dioxaphosphepine (L1),12 (Sa)-2-(phenoxy)-dinaph-
tho[2,1-d:1´,2´-f][1,3,2]dioxaphosphepine (L2),13 and
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14
[Ir(COD)Cl]2 were prepared according to the earlier pub-
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1a correspond to the literature data.15
Synthesis of 4-methyl-1,3-dihydro-2H-1,5-benzodiazepine-
2-one (1b). To a solution of acetyl chloride (0.1 mol, 7.8 g) in
diethyl ether (100 mL) cooled on an ice bath, triethylamine
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This work was financially supported by the Russian
Foundation for Basic Research (Project No. 17-03-00483).
Received September 23, 2016;
in revised form, February 28, 2017