95124-23-5

Upstream product

• 620-02-0 5-Methylfurfural 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 95124-39-3 4-methoxy-N-((5-methylfuran-2-yl)methyl)aniline 
• 112383-92-3 (3S,4S)-1-(4-Methoxy-phenyl)-4-(5-methyl-furan-2-yl)-3-phenoxy-azetidin-2-one 
• 1446516-56-8 C₁₅H₁₆N₂O₂ 
• 1446516-44-4 C₂₃H₂₀N₂O₅ 
• 95124-41-7 Picric acid; compound with (4-methoxy-phenyl)-(5-methyl-furan-2-ylmethyl)-amine 
• 95124-42-8 1-(4-Methoxy-phenyl)-1-(5-methyl-furan-2-ylmethyl)-3-phenyl-thiourea 

Relevant academic research and scientific papers

Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

The Murai reaction is a ruthenium-catalyzed transformation leading to alkylated arenes through the C?C bond formation between an alkene and an arene bearing a directing group. Discovered in the nineties, this useful C?H activation based coupling has been the object of intense study since its discovery. After having studied the Murai reaction on 2-formylfurans of biomass derivation, we describe here the carbonylative version applied to 2-formylfurans, 2-formylpyrrols and 2-formylthiophenes. This acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes thanks to the installation of removable imine directing groups. The transformation can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120–150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups. (Figure presented.).

Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant

A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.

METHODS FOR PREPARING ALKYLFURANS

Provided herein are methods for preparing alkylfurans, such as 2,5-dialkylfurans and 2-alkylfurans. Furfural or 5-alkylfurfural can be reacted with aniline or diaminobenzene, or derivatives thereof, to form the corresponding imine, which can be reduced to form alkylfurans and to regenerate the aniline or diaminobenzene, or derivatives thereof. The alkylfuran may be, for example, 2,5-dimethylfuran or 2-methylfuran.

Furan ring opening-pyrrole ring closure. A simple route to 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-3-ones

We report here an application of a furan ring opening-Paal-Knorr pyrrole synthesis sequence for the transformation of furfurylamines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-3-ones.

STUDIES IN THE FURAN SERIES. 22. N-ARYLFURFURYL- AND N-ARYL-5-METHYLFURFURYLAMINES AND THEIR N-ALLYL DERIVATIVES.

The compounds, where aryl is a meta- or para-substituted chlorophenyl, methoxyphenyl, or methylphenyl group, were prepared by reduction of corresponding azomethines. Their allylation with allyl iodide or allyl bromide yielded tertiary N-arylfurfurylamines