85658-02-2

Upstream product

• 75141-81-0 4-Nitro-3-(4-nitro-phenyl)-1-phenyl-butan-1-one 
• 85658-13-5 N-(α-Methyl-benzylidenamino)-4,6-diphenyl-2-pyridone 
• 98-86-2 acetophenone 
• 3672-66-0 1-(4-nitrophenyl)-3-phenylprop-2-yn-1-one 
• 99-81-0 4-Nitrophenacyl bromide 
• 85658-12-4 1-[4-Bromo-3-hydroxy-3-(4-nitro-phenyl)-1-phenyl-but-(E)-ylideneamino]-4,6-diphenyl-1H-pyridin-2-one 

Relevant academic research and scientific papers

Synthesis of 2,4-disubstituted furans and 4,6-diaryl-substituted 2,3-benzo-1,3a,6a-triazapentalenes

Reactions of acylacetylenes 1a-h with benzotriazole 2 give intermediates 3a-h. The treatment of 3a-h with trimethylsulfonium iodide in the presence of base give intermediate oxiranes 4a-h and 2,3-benzo-1,3a,6a-triazapentalenes 7d-g depending on substituent. Acid-catalyzed rearrangement of crude 4a-h give 2,4-disubstituted furans 5a-h.

Silylation of γ-nitro ketones as a convenient approach to the synthesis of 2-[N,N-bis(silyloxy)amino]-2,3-dihydrofurans and conjugated enoximes

Silylation of γ-nitro ketones of the general formula R 1COCH(R2)CH(R3)CH(R4)NO2 proceeded stereoselectively to give 2-[N,N-bis(trimethylsilyloxy)amino]-2,3- dihydrofurans, conjugated enoximes, silylation products of the carbonyl group or both functional groups, or N,N-bis(trimethylsilyloxy)enamine depending on the nature and positions of the substituents in the carbon skeleton. Dihydrofuran derivatives are formed for R1 = Ar or cyclo-C 3H5. Enoximes are generated as the silylation products of the starting ketones with enhanced β-proton mobility (R3 = CO2Me or 4-NO2C6H4). The presence of an alkyl group at the carbonyl function (R1 = Alk) is favorable for the formation of enoximes. Finally, the introduction of a substituent at the α position with respect to the nitro group (R4 = Me, CO2Me, or Ph) leads to the formation of silyl enolates. Under the action of NH4F in MeOH, dihydrofurans can be transformed into substituted furans in moderate yields.