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Synthesis of Substituted 2,3-Benzodiazepines
Chieh-Kai Chan1, Yu-Lin Tsai1, Yi-Ling Chan1
1Department of Medicinal and Applied Chemistry and General Research Centers of R&D Office, Kaohsiung Medical University , Kaohsiung 807, Taiwan.
The Journal of Organic Chemistry
|October 8, 2016
Abstract:
A new, four-step synthetic route for substituted 2,3-benzodiazepines 1, starting from aldehyde 4, was developed with excellent overall yields. This route included the 1,2-addition of various aromatic Grignard reagents to 4, PCC oxidation, and aerobic Wacker-type oxidation of the olefinic group of 6, followed by condensation of the resulting 1,5-dicarbonyl 7 with N2H4. Isoquinolones 9 were obtained when an aldehyde group was used instead of a ketone. The key structures were confirmed by X-ray single-crystal diffraction analysis.