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First synthesis of selenadiazolo[3,4‐ i ] Benzazepine derivatives
Author(s) -
Abou Elmaaty Tarek M.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450437
Subject(s) - chemistry , benzazepine , malononitrile , cyanoacetamide , methanol , dimethylformamide , acetal , organic chemistry , medicinal chemistry , bromide , ammonium acetate , ammonium , amine gas treating , high performance liquid chromatography , catalysis , solvent
5‐Methyl‐4‐nitro‐2,1,3‐benzoselenadiazole ( 1 ) was converted into ( E )‐5‐(2‐dimethylamino)vinylbenzo‐[ c ](1,2,5)selenadiazole‐4‐amine ( 4 ) by initial treatment with dimethylformamide dimethyl acetal (DMFDMA) ( 2 ) followed by selective reduction using ammonium bromide in methanol. Compound 4 afforded the selenadiazolo[3,4‐ i ][1]benzazepine derivatives ( 7, 10, 13, 15 ) upon treatment with malononitrile ( 5 ), ethyl cyanoacetate ( 8 ) and cyanoacetamide ( 11 ) respectively.