1749-14-0

Basic information

• Product Name: Benzenamine, N-(2-furanylmethylene)-4-methoxy-
• CAS NO: 1749-14-0
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.225
• Mol File: 1749-14-0.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-(2-furanylmethylene)-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-(2-furanylmethylene)-4-methoxy-(1749-14-0)
• EPA Substance Registry System: Benzenamine, N-(2-furanylmethylene)-4-methoxy-(1749-14-0)

Safety Data

• Hazardous Substances Data: 1749-14-0(Hazardous Substances Data)

Upstream product

• 98-01-1 furfural 
• 104-94-9 4-methoxy-aniline 
• 98-00-0 (2-furyl)methyl alcohol 
• 100-17-4 para-methoxynitrobenzene 
• 67-56-1 methanol 
• 62-53-3 aniline 
• 17377-97-8 N-(furan-2-ylmethyl)-4-methoxybenzenamine 

Downstream Products

• 17377-97-8 N-(furan-2-ylmethyl)-4-methoxybenzenamine 
• 50708-30-0 [2c-furan-2-yl-1-(4-methoxy-phenyl)-4-oxo-azetidin-3r-yl]-carbamic acid benzyl ester 
• 173416-01-8 N-(p-methoxyphenyl)-α-2-propenylfurylmethanamine 
• 31136-75-1 2-(furan-2-yl)-2-[(4-methoxyphenyl)amino]acetonitrile 
• 1048329-86-7 4-(4-methoxyphenylamino)-4-(furan-2-yl)butanenitrile 
• 1221718-05-3 C₁₉H₂₃NO₄ 
• 1448989-20-5 (2-furyl)-N-(4-methoxyphenyl)aminomethylphosphonic acid 
• 334708-42-8 [2R,3S,1'S,2'S]-(+)-3-(2-furyl)-3-(4-methoxyphenylamino)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'methylethyl)propanamide 

Relevant articles and documents

Polyoxometalate-Driven Ease Conversion of Valuable Furfural to trans- N, N-4,5-Diaminocyclopenten-2-ones

We investigated the catalytic efficacy of silicotungstic acid (H4SiW12O40) polyoxometalate (POM) toward the reaction between furfural and amines that selectively yields trans-N,N-4,5-substituted-diaminocyclopenten-2-ones (trans-DACPs). H4SiW12O40 facilita

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

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.).

Non-Bonding Electron Pair versus π-Electrons in Solution Phase Halogen Bond Catalysis: Povarov Reaction of 2-Vinylindoles and Imines

The non-bonding electron pair (n-pair) of heteroatoms and π-electrons are both efficient halogen bond (XB) acceptors. In solid and gas phase studies, n-pairs generally prevail over π-bonding orbitals as XB acceptors, whereas few studies have been conducte

Enantioselective Direct anti-Selective Mannich-type Reactions Catalyzed by 3-Pyrrolidinecarboxylic Acid in the Presence of Potassium Carbonate: Addition of Potassium Carbonate Improves Enantioselectivities

Mannich-type reactions of cyclohexanone and related six-membered-ring ketones with N-p-methoxyphenyl-protected imines of arylaldehydes catalyzed by 3-pyrrolidinecarboxylic acid in the presence of K2CO3 that afford anti-isomers of the Mannich products with

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is

Cationic allyl nickel complexes containing N,O-donor labile ligands: Synthesis and molecular characterisation

Three 2-iminofuran ligands 2-(N-2,6-diisopropylphenylformimino)furan (L1), 2-(N-2,6-dimethylphenylformimino)furan (L2) and 2-(N-4-methoxyphenylformimino)furan (L3) were obtained by condensation reactions of the respective anilines with furfural. The ηsup

Organocatalytic Mukaiyama Mannich Reactions of 2,5-Bis(trimethylsilyloxy)furan

The organocatalytic synthesis of densely substituted mono- and bis-?-lactams involving the Mukaiyama Mannich addition of 2,5-bis(trimethylsilyloxy)furan to imines is described. Use of a ditoluenesulfonylimide catalyst produces ?-lactams from monoaddition, whereas a more acidic catalyst (triflic acid) produces fused bis-lactams from double addition. Optimized organocatalytic conditions allow for the selective synthesis of either desired core as well as the one-pot, multicomponent assembly of the trisubstituted monolactams from aldehydes, amines, and bis-trimethylsilyloxyfuran. An examination of chiral acids found these organocatalysts to be highly active and diastereoselective in the monoaddition reaction, albeit with no enantioselectivity.

Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates

A Ru0-catalyzed direct C-H arylation and alkenylation of furfural imines with aryl- or alkenyl-boronates, in the presence of benzylideneacetone as a sacrificial hydride acceptor, is disclosed. This reaction provides access, after hydrolysis, to C3-arylated or vinylated furfural derivatives, and thus valorizes these relevant building-blocks obtained from lignocellulosic biomass. This approach, involving C-H activation by a Ru0/RuII, cycle offers several advantages, notably simple, mild and neutral reaction conditions.

One-pot sequential multicomponent reaction between: In situ generated aldimines and succinaldehyde: Facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles

An efficient sequential multi-component method for the synthesis of N-Arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and in situ generated Ar/H