Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones
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- 作者：Filip Křemen ; Martin Gazvoda ; Stanislav Kafka ; Karel Proisl ; Anna Srholcová ; Antonín Klásek ; Damijana Urankar ; Janez Košmrlj
- 刊名：Journal of Organic Chemistry
- 出版年：2017
- 出版时间：January 6, 2017
- 年：2017
- 卷：82
- 期：1
- 页码：715-722
- 全文大小：437K
- ISSN：1520-6904
文摘
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.