65027-11-4Relevant academic research and scientific papers
Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones
K?emen, Filip,Gazvoda, Martin,Kafka, Stanislav,Proisl, Karel,Srholcová, Anna,Klásek, Antonín,Urankar, Damijana,Ko?mrlj, Janez
, p. 715 - 722 (2017/04/26)
An unprecedented reactivity of 3-aminoquinoline-2,4-diones is reported. Under basic conditions, these compounds undergo molecular rearrangement to furnish 1,4-benzodiazepine-2,5-diones. The transformations take place under mild reaction conditions by using 1,1,3,3-tetramethylguanidine, NaOEt, or benzyltrimethylammonium hydroxide as a base. A proposed mechanism of the rearrangement and the conformational equilibrium of 1,4-benzodiazepine-2,5-dione rings are discussed.
Solid phase synthesis of 1,4-benzodiazepine-2,5-diones
Mayer, John P.,Zhang, Jingwen,Bjergarde, Kirsten,Lenz, Doug M.,Gaudino, John J.
, p. 8081 - 8084 (2007/10/03)
1,4-benzodiazepine-2,5-diones were synthesized by a simple procedure utilizing polymer supported amino acids and o-nitrobenzoic acids or protected anthranilic acids. Cyclization of the common aminoamide intermediate with concomitant release from the support furnished the desired 1,4-benzodiazepine-2,5-diones. The products were recovered in high yields and exhibited excellent purities.
New Synthesis of Diazepam and the Related 1,4-Benzodiazepines by means of Palladium-Catalyzed Carbonylation
Ishikura, Minoru,Mori, Miwako,Ikeda, Toshihito,Terashima, Masanao,Ban, Yoshio
, p. 2456 - 2461 (2007/10/02)
A new synthesis of diazepam (5) was achieved by application of palladium-catalyzed carbonylation to the compound 3 prepared from o-bromoaniline derivative 1 and the amino acid 2, and this procedure was also used for the synthesis of poisonous metabolites
