Abstract
New derivatives of 11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one have been synthesized. 11-(2-Thienyl)- and 11-(5-R-2-furyl)-substituted compounds were prepared by the Pictet–Spengler reaction of 3-amino-2-(3,4-dimethoxybenzyl)quinazolin-4(3H)-one with heterocyclic aldehydes in aprotic media. Their chemical structures were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry. We observed the opening of diazepine ring in 8,9-dimethoxy-11-(5-chloro-2-furyl)-11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one when treated with trifluoroacetic acid, and the structure of the product was determined by NMR (1H, 13C, HSQC, HMBC experiments) and mass spectrometry data. The crystal structure of 3-amino-2-[4,5-dimethoxy-2-[(5-oxofuran-2(5H)-yliden)methyl]benzyl]quinazolin-4(3H)-one was confirmed by single-crystal X-ray analysis.
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