39991-74-7

Upstream product

• 1460-08-8 2-diazocyclohexane-1,3-dione 
• 768-60-5 4-methoxyphenylacetylen 
• 60060-44-8 2-bromocyclohexane-1,3-dienone 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 866558-08-9 2-(4-methoxyphenyl)ethynyl-2-cyclohexen-1-one 

Downstream Products

• 36040-40-1 2-(4-methoxy-phenyl)-6-phenyl-4,5-dihydro-furo[2,3-c]acridine 
• 36154-84-4 2-(4-methoxy-phenyl)-6-methyl-4,5-dihydro-furo[2,3-c]acridine 
• 36040-43-4 2-(4-methoxy-phenyl)-6-phenyl-4,5-dihydro-benzo[a]furo[3,2-h]acridine 

Relevant academic research and scientific papers

Synthesis of oxazole and furan derivatives via Rh2(OAc)4-catalyzed C≡X bond insertion of cyclic 2-diazo-1,3-diketones with nitriles and arylacetylenes

A convenient and efficient procedure for the synthesis of 2-substituted-6,7-dihydrobenzo[d]oxazol-4(5H)-ones and 2-aryl-6,7-dihydrobenzofuran-4(5H)-ones through a Rh2(OAc)4-catalyzed C≡X (X = N, C) insertion of cyclic 2-diazo-1,3-diketones with nitriles and aromatic alkynes has been developed. This reaction uses readily available starting materials and stable cyclic 2-diazo-1,3-diketone compounds, with desired products formed in good to high yields. A tentative mechanism involving a C≡X bond insertion and 1,5-dipolar electrocyclization/ring opening and cyclization sequence for this reaction is proposed.

Chemoselectivity control: Gold(I)-catalyzed synthesis of 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans from 1-(alkynyl)-7- oxabicyclo[4.1.0]heptan-2-ones

New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products - 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans - could be obtained from the same starting material. The selectivity is determined by the ligand of the gold catalyst: triphenylphosphine delivers 6,7-dihydrobenzofuran-4(5H)-ones, and 1,3-bis(diisopropylphenyl)imidazol-2- ylidene leads to benzofurans. Eleven examples of each case are provided. The mechanistic suggestions for the pathways to both product types are supported by isotope labeling experiments. Complete chemoselectivity control of gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]heptan- 2-ones, which can be achieved by changing the ligand of the gold catalyst, allows two different products to be obtained from the same starting material, namely, 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans (see scheme), both of which are potent building blocks for synthetic chemistry. IPr: 1,3-bis(diisopropylphenyl)imidazol-2-ylidene. Copyright

De Novo synthesis of polysubstituted naphthols and furans using photoredox neutral coupling of alkynes with 2-bromo-1,3-dicarbonyl compounds

A conceptually new strategy has been described for the mild, practical, and environmentally friendly preparation of naphthols and furans using a visible-light promoted photoredox neutral approach. These reactions between accessible electron-deficient bromides and commercially available alkynes could be carried out at room temperature in good-to-excellent chemical yields without any external stoichiometric oxidants.