356539-11-2

Upstream product

• 56106-05-9 N-(4-methoxyphenyl)succinamic acid 
• 109-99-9 tetrahydrofuran 
• 104-94-9 4-methoxy-aniline 
• 14990-93-3 N-(4-methoxyphenyl)-2-pyridinecarboxamide 
• 100-17-4 para-methoxynitrobenzene 
• 13325-10-5 4-Aminobutanol 
• 696-62-8 para-iodoanisole 

Downstream Products

• 1009557-46-3 (4-hydroxybutyl)(4-methoxyphenyl)carbamic acid phenyl ester 

Relevant academic research and scientific papers

N-arylation method in aqueous phase system with substituted quinoline or isoquinoyl hydrazide pyridine-N-oxide as ligand

The invention relates to an N-arylation method in an aqueous phase system with substituted quinoline or isoquinoyl hydrazide pyridine-N-oxide as a ligand. The N-arylation method in the aqueous phase system with the substituted quinoline or isoquinoyl hydrazide pyridine-N-oxide as the ligand comprises the following steps of: adding a catalyst, the ligand, a raw material, alkali, a phase transferring catalyst and a solvent into a reactor, heating and stirring, after the reaction is ended, separating and purifying a reaction solution to obtain an N-arylation product, wherein the raw material is aryl halide and a nitrogen-containing nucleophilic reagent, the solvent is a mixed solution of water and ethanol, and the catalyst is metal copper, or a copper oxide, or monovalent copper salt, or bivalent copper salt. The N-arylation method in the aqueous phase system with substituted quinoline or isoquinoyl hydrazide pyridine-N-oxide as the ligand has the characteristics of simplicity in operation, wide substrate application range, simplicity and easiness in separating products, high yield, economical process, environmental protection and the like.

Cu2O/1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide catalyzed C-N cross-coupling reaction in aqueous media

An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of imidazole, indole, pyrrole, alkyl alcohol amines, and alkyl amines with aryl iodides and bromides. The reaction proceeds in water-ethanol media at 120 °C for 12 h with Cu2O as the catalyst, 1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide (L2) as the ligand, NaOH as the base to generate a wide range of N-arylated products in moderate to excellent yields. Aqueous medium, ease of operation, and broad substrate scope give the process a benign environmental profile.

An efficient and atom-economical route to: N -aryl amino alcohols from primary amines

In this paper we reported a novel method for generation of N-aryl amino alcohols from N,N-disubstituted picolinamides through reduction/ring-opening reaction with NaBH4. The N,N-disubstituted picolinamides can be easily obtained from primary am

Formation of 4-N-arylamino-1-butanol derivatives from aromatic nitro compounds via a novel palladium-catalyzed tetrahydrofuran ring-opening reaction

4-N-Arylamino-1-butanol derivatives are produced via a palladium-catalyzed tetrahydrofuran ring-opening reaction. This reaction occurs during the reduction of aromatic nitro groups with polymethylhydrosiloxane (PMHS) and potassium fluoride in the presence of hydrogen peroxide. This represents a novel route for the synthesis of 4-N-arylamino-1-butanols.

Asymmetric synthesis of cyclic α-amino acid derivatives by the intramolecular reaction of magnesium carbenoid with an N-magnesio arylamine

The synthesis of pipecolic acid and homopipecolic acid derivatives was developed from ω-(2-aminophenyl)-1-chloroalkyl p-tolyl sulfoxides by treatment with i-PrMgCl. An intramolecular nucleophilic substitution reaction of a magnesium carbenoid with an N-magnesio arylamine is the key step of this reaction. Proline and pipecolic acid derivatives were also synthesized from ω-(arylamino)-1-chloroalkyl p-tolyl sulfoxides by the same chemistry. Starting from enantiomerically pure (1S,RS)-1-chloro-3-[2-(N-methylamino)phenyl]propyl p-tolyl sulfoxide, enantiomerically pure (R)-pipecolic acid derivative was obtained. The intramolecular nucleophilic substitution reaction of the magnesium carbenoid with N-magnesio arylamine was proven to take place with inversion of the carbenoid carbon. The stereochemistry of these reactions is also discussed.

Synthesis of diverse 2,3-dihydroindoles, 1,2,3,4-tetrahydroquinolines, and benzo-fused azepines by formal radical cyclization onto aromatic rings

(Chemical Equation Presented) 2,3-Dihydroindoles, 1,2,3,4- tetrahydroquinolines, and 2,3,4,5-tetrahydrobenzo[b]azepines are available by a process that represents formal radical cyclization onto aromatic rings. Optically pure benzo-fused heterocycles are also accessible by this method. p-Iodophenols, especially those with the phenolic oxygen protected as a MOM-ether, can be coupled with amino alcohols to produce N-aryl amino alcohols, which can be converted into the corresponding alkyl iodides in which the nitrogen is protected as a carbamate. These compounds give cross-conjugated ketones after removal of the phenolic protecting group and oxidation with PhI(OAc)2 in the presence of MeOH. The ketones undergo 5-, 6- or 7-exo-trigonal radical cyclization, and then exposure to acid, or sequential treatment with a Grignard reagent and then acid, effects rearomatization to produce the benzo-fused nitrogen heterocycles.

A new palladium-mediated approach to 4-N-arylamino-1-butanols from peroxidic tetrahydrofuran and primary aromatic amines

Reaction of primary aromatic amines with peroxidic tetrahydrofuran (THF) in the presence of hydrogen and 10% palladium on carbon catalyst results in THF ring opening to give 4-N-arylamino-1-butanols in a good yield. The reaction mechanism is believed to i

Investigation into the structure-activity relationship of novel concentration dependent, dual action T-type calcium channel agonists/antagonists

This paper describes the synthesis and biological evaluation of a series of straight chain analogs of a compound (1) that was previously synthesized in our research program. These compounds, which are T-type calcium channel antagonists, exhibits potent anti-proliferative activity against a variety of cancer cells. A structure-activity relationship of these analogs against a variety of cancer cells has provided insight into a logical pharmacophore for this series of compounds. Furthermore, this series of compounds has presented itself as a set of novel, concentration dependent, dual action agonists/antagonists for the T-type calcium channel.