Synthesis of aromatic derivatives of 1,5-benzodiazepine in the reaction of 4-nitro-o-phenylenediamine with chalcone dibromides

Investigations on 5-(2-aryl-2-oxo-ethylidene)-1,3-dimethylbarbituric and thiobarbituric acids: reactions with thioureas and thioacetamide

“…Such a hypothesis is in good agreement with the data obtained by us previously for reactions of enones with a series of azabinucleophiles [9][10][11].…”

Synthetic Utilization of α,β‐Chalcone Dibromide In Heterocyclic Chemistry and Stereoselective Debromination

“…Struchkov and his co‐workers examined the reaction of 1‐aryl‐3‐( p ‐nitrophenyl)‐2,3‐dibromopropenone 2 with 4‐nitro‐o‐phenylenediamine 22 under different reaction condition. The reaction result reveals that 4‐nitro‐l‐( p ‐nitrophenyl)‐8‐aryl‐1,8a‐dihydroazirino[1,2‐a]quinoxalines 24 obtained via γ‐elimination of HBr from 23 in less than 10% yield under milder basic condition whereas 3 equivalent of triethylamine led to β‐(2‐amino‐4‐nitroanilino)chalcones 25 via dehydrobromination of intermediate 23 and these chalcone was further utilized to synthesize the 2,4‐diaryl‐7(8)‐nitro‐l,5‐benzodiazepines 26 (Scheme ) . Mixture of 1,1a‐dihydroazirino[1,2‐a]quinoxaline 24 f and β‐(2‐amino‐4‐nitroanilino)‐4‐nitrochalcone 25 f was obtained when reaction of 4‐nitro‐o‐phenylenediamine 22 performed with 3‐( p ‐nitrophenyl)‐l‐phenyl‐2,3‐dibromopropenone 2 f in presence of basic catalyst.…”

Chalcone derived benzoheterodiazepines for medicinal applications: A Two‐pot and one‐pot synthetic approach

“…Benzoheterodiazepine derivatives are designed from different reactants such as cinnamoylacetonitrile [64], hydrazone [65], flavone [66], chalcone [67], α-haloketones [68,69], ethyl acetoacetate [70], cinnamoyl cyanide [71], propargylic alcohols [72], or ketones [73][74][75]. The condensation of diamines (i.e., o-phenylenediamine, o-aminothiophenol, o-aminophenol) and chalcones [76,77] is common under different modes of reactions (i.e., stirring [78], grindstone [79], reflux [80,81], MW [82,83], and ultrasonic irradiations [84,85]) in the presence of catalysts (i.e., piperidine [86,87], NaOH [88,89], NaOAc [90], acetic acid [91,92], trifluoroacetic acid [93], InCl 3 [94], alumina [82], volcanic ash [95], Ti(OiPr) 4 [77], MgO-ZrO 2 [96], SmI 2 [78], SiO 2 [97], Al 2 O 3 [80], TiCl 4 /Sm [98], Bi(NO 3 ) 3 -Al 2 O 3 [99], La Y zeolite [100], HClO 4 -SiO 2 [101], Fe 3 O 4 [102], B(HSO 4 ) 3 …”