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Synthesis of isoquinobenzodiazepinediones
Author(s) -
GÁllIstÓk KlÁra,
Sterk Lili,
TÓth GÁbor,
Deák Gyula
Publication year - 1984
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.5570210424
Subject(s) - chemistry , sodium hydride , dimethyl sulfate , yield (engineering) , anhydrous , medicinal chemistry , benzodiazepine , organic chemistry , materials science , metallurgy , biochemistry , receptor
1‐(2′‐Chloroacetylamino)‐4,4‐dimethyl‐1,4‐dihydro‐3(2 H )‐isoquinolinone ( 3 ) was cyclised by treatment with sodium hydride in dimethyl sulphoxide containing 0.1 % of water to give 10,10‐dimethyl‐6,7,9,10‐tetrahydro‐5 H ,14b H ‐isoquino[2,1‐ d ][1,4]benzodiazepine‐6,9‐dione ( 4 ) in a yield of 80%. In anhydrous dimethyl sulphoxide the main product of the reaction was 5‐ N ‐(4,4‐dimethyl‐1‐phenyl‐1,4‐dihydro‐3(2 H )‐isoquinolinon‐1′‐yl)isoquino[2,1‐ d ][1,4]benzodiazepine‐6,9‐dione ( 5 ), which was also prepared by the reaction of 3 with 4 .