60336-05-2

Upstream product

• 52938-97-3 5-phenylfuran-2-carboxylic acid 
• 64-17-5 ethanol 
• 1354642-83-3 ethyl 2,5-dioxo-5-phenylpentanoate 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 623-73-4 diazoacetic acid ethyl ester 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 
• 6132-37-2 ethyl 5-bromofuran-2-carboxylate 
• 603-33-8 triphenylbismuthane 

Relevant academic research and scientific papers

Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor-Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates

A direct synthetic strategy starting from alkyl 1-alkoxy-2-aroylcyclopropanecarboxylates was developed for the construction of alkyl 5-arylfuran-2-carboxylates. These donor-acceptor cyclopropanes smoothly undergo a simple ring-opening reaction or/and cycl

Copper(I)-catalyzed A3-coupling based reaction of alkynes, aldehydes, and amines: An efficient approach to 2,5-polysubstituted dihydrofurans and 2,5-disubstituted furans

Abstract An efficient and practical A3-coupling based reaction that gives a variety of 2,5-polysubstituted dihydrofurans and 2,5-disubstituted furan derivatives has been developed. This domino copper-catalyzed three-component coupling reaction of propargylic alcohol, ethyl glyoxalate, and an amine affords a propargylic amine intermediate, which undergoes an alkyne-allene isomerization followed by a cyclization to yield the dihydrofuran. Upon treatment with CH3I and base, the latter was smoothly converted into a 2,5-disubstituted furan. Alternatively, the furan derivatives can be directly prepared by a two-step reaction sequence. An efficient and practical A3-coupling based reaction that gives a variety of 2,5-polysubstituted dihydrofurans has been developed. The starting materials are commercially available, and the reaction conditions are mild. In addition, 2,5-disubstituted furans can be prepared by treating the dihydrofuran derivatives with CH3I and base in a two-step reaction sequence.

Reactions of enaminones with diazocarbonyl compounds

The [Cu(acac)2]-catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino- and additionally carbonyl-substituted dihydrofurans, together with further furan derivatives. Due to the conjugation of α-carbonyl/α-Ph groups, reactions proceeded only via 1,5-electrocyclization of corresponding keto-ylides. On the other hand, in the absence of any α-substituent, tertiary enaminone and ethyl diazoacetate, reacted via an accompanying mechanism by a push-pull cyclopropane intermediate, to yield a 2,4-dicarbonyl-substituted furan in one step with moderate yield. Copyright

Mono- and biscouplings using triarylbismuths for the atom-efficient arylations of functionalized furans under palladium catalysis

Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one hour). Georg Thieme Verlag Stuttgart · New York.

Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: Successive Amberlyst A21- and Amberlyst 15-catalyzed processes

The nitroaldol reaction of ketal-functionalized nitroalkanes with α-oxoaldehydes, promoted by Amberlyst A21, followed by acidic treatment (Amberlyst 15) of the obtained nitroalkanol, leads to the formation of 2,5-disubstituted furans in good yields. The p

One-step synthesis of 5-acylisothiazoles from furans

Premixed ethyl carbamate, thionyl chloride and pyridine (which generate thiazyl chloride, N≡SCl) in boiling benzene or toluene convert 2,5- and 2,3,5-substituted furans into 5-acylisothiazoles regiospecifically. The reactions are much faster and generally higher yielding in boiling chlorobenzene with more thionyl chloride and with pyridine or isoquinoline as base. Under the more vigorous conditions, even fully substituted 3-bromofurans give isothiazoles, with the displacement of bromine. Deactivated furans, with electron-withdrawing groups such as ester, cyano, benzoyl and phenylsulfonyl in the α-position, react under the more vigorous conditions to give 5-acylisothiazoles with the electronegative group in the 3-position. The 'activated' 2-methyl-5-phenyl- and 5-phenyl-2-phenylthio-furans react analogously, with the more electron-releasing group becoming part of the 5-acyl substituent, exclusively or predominantly. These results are explained by initial electrophilic attack of the furan ring to give a β-thiazyl derivative which spontaneously ring-opens and closes to the isothiazole. The X-ray structures of five of the differently substituted isothiazole compounds are reported. All have very similar patterns of bonding within their isothiazole rings that appear to be independent of the electron-withdrawing or -donating nature of the substituents. Three of the compounds (8a, 8g and 13) have loosely linked chain structures in the solid state, adjacent molecules being connected by combinations of hydrogen bonding and π-π stacking interactions.