17377-97-8

Usage

Uses

Furan-2-ylmethyl-(4-methoxy-phenyl)-amine is used as a chemical intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries. Its unique structure allows it to be a key component in the development of new molecules with potential applications in drug discovery and material science.
Used in Pharmaceutical Industry:
Furan-2-ylmethyl-(4-methoxy-phenyl)-amine is used as a building block for the creation of novel drug candidates, leveraging its structural diversity to explore new therapeutic avenues. Its presence in a molecule can influence the compound's pharmacokinetic and pharmacodynamic properties, making it a valuable asset in the design of innovative medications.
Used in Chemical Research and Development:
Furan-2-ylmethyl-(4-methoxy-phenyl)-amine is used as a research tool in the exploration of new chemical reactions and mechanisms. Its incorporation into experimental compounds can provide insights into the reactivity and stability of molecules, contributing to the advancement of organic chemistry and related fields.
Used in Material Science:
Furan-2-ylmethyl-(4-methoxy-phenyl)-amine is used as a component in the development of new materials with unique properties, such as improved conductivity, stability, or reactivity. Its incorporation into polymers or other materials can lead to the creation of innovative products with applications in various industries, including electronics, energy, and environmental protection.

InChI:InChI=1/C13H13N3.C8H6O4/c14-13(15)16(11-7-3-1-4-8-11)12-9-5-2-6-10-12;9-7(10)5-3-1-2-4-6(5)8(11)12/h1-10H,(H3,14,15);1-4H,(H,9,10)(H,11,12)

Upstream product

• 617-89-0 furan-2-ylmethanamine 
• 623-12-1 4-chloromethoxybenzene 
• 10257-32-6 D-ribose 
• 87-72-9 L-(+)-arabinose 
• 2460-44-8 β-D-xylopyranoside 
• 19820-47-4 4-methoxyphenyl 2,2-dimethylpropionate 
• 98-01-1 furfural 
• 98-00-0 (2-furyl)methyl alcohol 
• 104-94-9 4-methoxy-aniline 
• 100239-11-0 (E)-N-2-furylidene-4-methoxyaniline 
• 1749-14-0 N-furfurylidene-p-anisidine 

Downstream Products

• 17960-79-1 2-(4-methoxy-phenyl)-1,2,3,6,7,7a-hexahydro-3a,6-epioxido-isoindole 
• 114142-96-0 6-[Furan-2-ylmethyl-(4-methoxy-phenyl)-amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 17960-71-3 N-allyl-N-furfuryl-4-methoxy-aniline 
• 1027430-46-1 (2S,3S)-3-Furan-2-yl-3-(4-methoxy-phenylamino)-2-methyl-propionaldehyde 
• 1749-14-0 N-furfurylidene-p-anisidine 
• 114143-02-1 6-[Furan-2-ylmethyl-(4-methoxy-phenyl)-amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde oxime 
• 114143-13-4 11-(4-Methoxy-phenyl)-1,3-dimethyl-10,11-dihydro-1H,6aH-6,9-dioxa-1,3,5,11-tetraaza-pentaleno[1,6a-a]naphthalene-2,4-dione 
• 100239-11-0 (E)-N-2-furylidene-4-methoxyaniline 

Relevant academic research and scientific papers

PAd2-DalPhos Enables the Nickel-Catalyzed C?N Cross-Coupling of Primary Heteroarylamines and (Hetero)aryl Chlorides

Base-metal catalysts capable of enabling the assembly of heteroatom-dense molecules by cross-coupling of primary heteroarylamines and (hetero)aryl chlorides, while sought-after given the ubiquity of unsymmetrical di(hetero)arylamino fragments in pharmacophores, are unknown. Herein, we disclose the new “double cage” bisphosphine PAd2-DalPhos (L2). The derived air-stable NiII pre-catalyst C2 functions well at low loadings in challenging test C?N cross-couplings with established substrates, and facilitates the first Ni-catalyzed C?N cross-couplings of primary five- or six-membered ring heteroarylamines and activated (hetero)aryl chlorides, with synthetically useful scope that is competitive with Pd catalysis.

Examining the Impact of Heteroaryl Variants of PAd-DalPhos on Nickel-Catalyzed C(sp2)-N Cross-Couplings

We report herein on the synthesis of new heteroaryl analogues of PAd-DalPhos and related bis(di(o-tolyl)phosphino) ancillary ligand variants based on pyridine or thiophene backbone structures, and their application in nickel-catalyzed C(sp2)-N cross-couplings under challenging reaction conditions. The 3,4-disubstituted thiophene-based ancillary ligand ThioPAd-DalPhos (L8) was observed to be particularly effective in the nickel-catalyzed C(sp2)-N cross-coupling of primary alkylamines, and the derived precatalyst (L8)NiCl(o-tolyl) (C2) was found to offer improved performance versus the related PAd-DalPhos-derived precatalyst C1 in such transformations. In using C2, cross-couplings of various primary alkylamines and (hetero)aryl-X electrophiles (X = Cl, Br, OTs) proceeded under unprecedentedly mild reaction conditions (0.25-0.50 mol % Ni), including examples conducted at room temperature. Also reported herein are the results of our combined experimental/DFT computational study directed toward gaining insight regarding the improved catalytic performance of C2 versus C1.

Novel N-Alkylbenzimidazole-Ruthenium (II) complexes: Synthesis and catalytic activity of N-alkylating reaction under solvent-free medium

In this article, direct N-alkylation reactions of amines with alcohols derivatives have been investigated. For this purpose, a new series ruthenium (II) complexes bearing N-coordinated benzimidazole complexes with have been synthesized and fully characterized by elemental analysis, FT-IR, 1H NMR and, 13C NMR spectroscopies. Additionally, the structures of the complexes 2b and 2c have been confirmed by X-ray crystallography. Although the N-alkylating reaction is usually performed in toluene, the catalytic study of complexes 2a-d has carried out no additional solvent and alcohol acted both as solvent and reactant of alkylating by using a little excess of alcohols. Surprisingly, conversion and selectivity of amine product for alkylation reaction have been seen high in medium solvent-free relative to in toluene.

Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations

Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.

A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels-Alder Reaction: Stereoselective Synthesis of Octahydro-1 H-cyclopenta[ cd]isoindole

For the first time, an efficient one-pot method for the construction of an angularly fused 5-6-5 aza-tricyclic framework has been developed in a highly stereoselective manner. This domino reaction is a novel combination of aza-Piancatelli rearrangement an

One-pot synthesis of amines from biomass resources catalyzed by HReO4

This work describes the one-pot synthesis of furfurylamines from carbohydrates catalyzed by HReO4. These one-pot three-reaction and four-reaction processes allow the conversion of xylose and xylan, respectively, into a large variety of secondary and tertiary amines with good overall yields and chemoselectivity.

A simple method for the synthesis of 1,3-diaminopropan-2-ols derivatives and their ex vivo relaxant activity on isolated rat tracheal rings

Abstract: A mild and eco-friendly method has been developed for the synthesis of a series of 1,3-diaminopropan-2-ols 8a–n. The epoxide of epichlorohydrin undergoes ring-opening with amines using MgSO4 or mixed metal oxides catalysts under mild

Nickel-Catalyzed Cross-Coupling of Ammonia or Primary Alkylamines with (Hetero)aryl Sulfamates, Carbamates, or Pivalates

A catalyst system capable of effecting the cross-coupling of ammonia or primary alkylamines with (hetero)aryl sulfamates, carbamates, or pivalates is reported for the first time. The air-stable nickel(II) pre-catalyst C1 tolerates a broad spectrum of heterocyclic functionality within both reaction partners, as well as ether, nitrile, pyrrole, trifluoromethyl, and boronate ester substituents. In the case of reactions involving primary alkylamines and (hetero)aryl sulfamates and carbamates, room-temperature cross-couplings were achieved.

A comparative reactivity survey of some prominent bisphosphine nickel(II) precatalysts in C-N cross-coupling

The synthesis and characterization of the new air-stable precatalyst (L1)Ni(o-tol)Cl (C1; where L1 = JosiPhos CyPF-Cy) is reported, along with the results of a comparative reactivity survey involving C1 and analogous PAd-DalPhos- and DPPF-containing precatalysts (C2 and C3, respectively) in representative nickel-catalyzed C(sp2)-N cross-coupling reactions. Precatalyst C1 was found to be competitive with, and in some cases complementary to, C2 in the monoarylation of ammonia and primary alkylamines with (hetero)aryl chlorides, including in otherwise challenging room temperature transformations. (Pseudo)halide comparison studies involving the cross-coupling of furfurylamine at room temperature revealed that in contrast to C2 precatalyst C1 performs less effectively with aryl bromides. Whereas C3 was found to be ineffective for such transformations, this DPPF-derived precatalyst proved superior to C1 and C2 in reactions involving the secondary dialkylamine test substrate morpholine.