%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