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Synthesis of 1,4-benzodiazepine-2,5-diones by base promoted ring expansion of 3-aminoquinoline-2,4-diones
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| Title: | Synthesis of 1,4-benzodiazepine-2,5-diones by base promoted ring expansion of 3-aminoquinoline-2,4-diones | ||||||||||
| Author: | Křemen, Filip; Gazvoda, Martin; Kafka, Stanislav; Proisl, Karel; Srholcová, Anna; Klásek, Antonín; Urankar, Damijana; Košmrlj, Janez | ||||||||||
| Document type: | Peer-reviewed article (English) | ||||||||||
| Source document: | Journal of Organic Chemistry. 2017, vol. 82, issue 1, p. 715-722 | ||||||||||
| ISSN: | 0022-3263 (Sherpa/RoMEO, JCR) | ||||||||||
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| DOI: | https://doi.org/10.1021/acs.joc.6b01497 | ||||||||||
| Abstract: | 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. | ||||||||||
| Full text: | http://pubs.acs.org/doi/full/10.1021/acs.joc.6b01497 | ||||||||||
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ČSN ISO 690:2011 citation
Citace článku v časopise:
KŘEMEN, Filip, Martin GAZVODA, Stanislav KAFKA, Karel PROISL, Anna SRHOLCOVÁ, Antonín KLÁSEK, Damijana URANKAR a Janez KOŠMRLJ. Synthesis of 1,4-benzodiazepine-2,5-diones by base promoted ring expansion of 3-aminoquinoline-2,4-diones. Journal of Organic Chemistry [online]. 2017, vol. 82, iss. 1, s. 715-722. [cit. 2024-04-19]. ISSN 0022-3263. Dostupné z: http://pubs.acs.org/doi/full/10.1021/acs.joc.6b01497.
These citations are software generated and may contain errors. To verify accuracy, check the appropriate style guide.
KŘEMEN, Filip, Martin GAZVODA, Stanislav KAFKA, Karel PROISL, Anna SRHOLCOVÁ, Antonín KLÁSEK, Damijana URANKAR a Janez KOŠMRLJ. Synthesis of 1,4-benzodiazepine-2,5-diones by base promoted ring expansion of 3-aminoquinoline-2,4-diones. Journal of Organic Chemistry [online]. 2017, vol. 82, iss. 1, s. 715-722. [cit. 2024-04-19]. ISSN 0022-3263. Dostupné z: http://pubs.acs.org/doi/full/10.1021/acs.joc.6b01497.
These citations are software generated and may contain errors. To verify accuracy, check the appropriate style guide.
