%0 Journal Article %A Chan, Chieh-Kai %A Tsai, Yu-Lin %A Chan, Yi-Ling %A Chang, Meng-Yang %D 2016 %T Synthesis of Substituted 2,3-Benzodiazepines %U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Substituted_2_3-Benzodiazepines/4019598 %R 10.1021/acs.joc.6b01935.s006 %2 https://acs.figshare.com/ndownloader/files/6474492 %K PCC oxidation %K Benzodiazepine %K olefinic group %K four-step %K N 2 H 4 %K aldehyde group %K dicarbonyl %K Substituted %K Isoquinolones 9 %K Synthesi %K benzodiazepines %K X-ray single-crystal diffraction analysis %K condensation %K Wacker-type oxidation %K Grignard reagents %K yield %K aldehyde 4 %K ketone %X 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. %I ACS Publications