50800-39-0

Upstream product

• 81661-27-0 ethyl 2-phenyl-5-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-3-furoate 
• 92190-57-3 ethyl(2-benzoylpent-4-ynoate) 
• 107-19-7 propargyl alcohol 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 83554-53-4 2-phenyl-5-(phenylhydrazono-methyl)-furan-3-carboxylic acid ethyl ester 
• 81661-25-8 2-phenyl-furan-3,5-dicarboxylic acid 

Relevant academic research and scientific papers

Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters

Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ3-iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl- λ3-iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ3-iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.

PIFA-mediated oxidative cycloisomerization of 2-propargyl-1,3-dicarbonyl compounds: Divergent synthesis of furfuryl alcohols and furfurals

PhI(OCOCF3)2 (PIFA) in the presence of trifluoroacetic acid (TFA) in CH2Cl2 efficiently promotes the oxidative cycloisomerization of 2-propargyl 1,3-dicarbonyl compounds to give 4,5-disubstituted furfuryl alcoho

Transition-metal-catalyzed domino reactions: Efficient one-pot regiospecific synthesis of highly functionalized polysubstituted furans from electron-deficient alkynes and 2-Yn-1-ols

Based on the reactive behavior of different transition-metal catalysts, three methods for the synthesis of highly functionalized polysubstituted furan derivatives are presented: (i) copper(I) iodide catalyzed regiospecific synthesis of furan aldehydes/ketones from alkynols and diethyl but-2-ynedioate under atmospheric pressure; (ii) nano-Cu-catalyzed domino process for the regioselective synthesis of -carbonylfurans from readily accessible starting materials; (iii) silver-catalyzed one-pot cyclization in toluene at 50 C for the synthesis of furan derivatives. It was notably that all the domino reactions were smooth under mild conditions with commercially available catalysts, and afforded highly functionalized furans in moderate to good yields. As we know, furans derivatives are extremely useful organic molecules used as synthetic building blocks for the synthesis of more elaborate heterocyclic compounds. Georg Thieme Verlag Stuttgart.

Iron-catalyzed domino process for the synthesis of α-carbonyl furan derivatives via one-pot cyclization reaction

(Figure presented) The Fe(ClO4)3-catalyzed intramolecular rearrangement/cyclization/oxidation reaction sequence for the synthesis of α-carbonyl furan derivatives from electron-deficient alkynes and 2-yn-1-ols is reported.

Nano-Cu2O-catalyzed formation of C-C and C-O bonds: One-pot domino process for regioselective synthesis of α-carbonyl furans from electron-deficient alkynes and 2-Yn-1-ols

The formation of carboncarbon and carbon-oxygen bonds continues to be an active and challenging field of chemical research. Nanoparticle catalysis has attracted considerable attention owing to its environmentally benign and high activity toward the reactions. Herein, we described a novel and effective nano-Cu2O-catalyzed one-pot domino process for the regioselective synthesis of α-carbonyl furans. Various electron-deficient alkynes with 2-yn-1-ols underwent this process smoothly in moderate to good yields in the presence of air at atmospheric pressure. It is especially noteworthy that a novel 2,4,5-trisubstituted 3-ynylfuran was formed in an extremely direct manner without tedious stepwise synthesis. Additionally, as all of the starting materials are readily available, this method may allow the synthesis of more complex α-carbonyl furans. An experiment to elucidate the mechanism suggested that the process involved a carbene intermediate.

PREPARATION OF FURAN DERIVATES FROM PENTOSES AND HEXOSES. STUDY OF THE ANHYDRIZATION OF THE TETRAHYDROXYLATED CHAIN AT α POSITION

The reaction of pentoses and hexoses with active methylene compounds in presence of an ethanolic solution of a Lewis acid or mixtures of aquenous acids leads to polyfunctional furanic derivatives in wich a polyhydroxylated chain exists in α position.When