234443-67-5

Basic information

• Product Name: 2H-Furo[2,3-b]pyrrol-3(4H)-one, 5,6-dihydro-6-phenyl- (9CI)
• Synonyms: 2H-Furo[2,3-b]pyrrol-3(4H)-one, 5,6-dihydro-6-phenyl- (9CI)
• CAS NO: 234443-67-5
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.22
• Mol File: 234443-67-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Furo[2,3-b]pyrrol-3(4H)-one, 5,6-dihydro-6-phenyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Furo[2,3-b]pyrrol-3(4H)-one, 5,6-dihydro-6-phenyl- (9CI)(234443-67-5)
• EPA Substance Registry System: 2H-Furo[2,3-b]pyrrol-3(4H)-one, 5,6-dihydro-6-phenyl- (9CI)(234443-67-5)

Safety Data

• Hazardous Substances Data: 234443-67-5(Hazardous Substances Data)

Upstream product

• 234443-66-4 3-diazoacetyl-2-oxo-1-phenylpyrrolidine 
• 56137-52-1 1-phenyl-2-oxo-3-pyrrolidine-3-carboxylic acid 

Relevant articles and documents

A push-pull carbonyl ylide cycloaddition approach directed toward lycorine

Cyclic 2-amidofurans were obtained using a Rh(II)-catalyzed reaction of α-diazoketo substituted pyrrolidinone derivatives. Acylation followed by a Diels-Alder reaction of the resulting amidofuran furnished both inter and intramolecular cycloadducts.

Cyclization-cycloaddition cascades for the construction of azapolycyclic ring systems

Cyclic 2-amidofuranones were obtained from the Rh(II)-catalyzed reaction of α-diazoketo substituted pyrrolidine derivatives. These compounds are derived by a [1,4]-hydrogen transfer from an initially formed carbonyl ylide dipole. Acylation of the amido-substituted furanone with pivalyl chloride provided a fused amidofuran, which underwent bimolecular Diels-Alder cycloaddition with N-phenylmaleimide. The Rh(II)-catalyzed decomposition of ethyl 2-diazo-3-oxo-(2-oxo-1-pent-4-enoyl-pyrrolidine-3-yl)propionate was also examined. In this case, the alkenyl group tethered to the amido carbonyl underwent smooth intramolecular [4+2]-cycloaddition with the amidofuran obtained from the acylation reaction. An alternate route for the synthesis of cyclic amidofurans was developed using a Pummerer induced cyclization of the thiophenyl substituted acetal derived from the aldol reaction of methoxyphenylsulfanyl acetaldehyde with α-valerolactam. Treatment of the amido-substituted acetal with dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) generated an oxonium ion, which readily cyclized onto the adjacent carbonyl group. The amidofuran that was formed underwent an intramolecular Diels-Alder reaction when heated at 110°C in toluene. Subsequent ring opening of the transient [4+2]-cycloadduct followed by elimination of methanol and tautomerization of the resulting cyclohexadienone gave rise to the observed phenolic lactam in good overall yield.