Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 1, Pages 715-722Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01497
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Funding
- TBU in Zlin [IGA/FT/2016/004]
- Ministry of Education, Science, and Sport, Republic of Slovenia, the Slovenian Research Agency [P1-0230]
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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.
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