14227-17-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 682, 1994 DOI: 10.1021/jo00082a035

InChI:InChI=1/C9H13NO3/c1-11-6-4-7(12-2)9(10)8(5-6)13-3/h4-5H,10H2,1-3H3

Upstream product

• 14227-18-0 1,3,5-trimethoxy-2-nitrobenzene 
• 102438-99-3 2,4,6-trimethoxyaniline hydrochloride 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 621-23-8 1,2,3-trimethoxybenzene 
• 600121-36-6 (1,3-dimethyl-imidazolidin-2-ylidene)-(2,4,6-trimethoxy-phenyl)-amine 
• 148678-90-4 1-(2,4,6-trimethoxyphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester 
• 17483-54-4 2,4,6-trimethoxybenzamide 

Downstream Products

• 115591-40-7 N-formyl-2,4,6-trimethoxyaniline 
• 122705-93-5 (Z)-N-(2,4,6-trimethoxyphenyl)-9-octadecenamide 
• 143593-10-6 5-Phenyl-1-(2,4,6-trimethoxy-phenyl)-pyrrolidine-2,2-diol 
• 140112-83-0 N-(2,4,6-trimethoxyphenyl)stearamide 
• 1028285-87-1 2-Benzylsulfanyl-N-(2,4,6-trimethoxy-phenyl)-nicotinamide 
• 148926-60-7 (1) 2-dodecyl-α-phenyl-N-(2,4,6-trimethoxyphenyl)-2H-tetrazole-5-acetamide 

Relevant academic research and scientific papers

PRODUCTION METHOD OF PRIMARY AMINE COMPOUND

PROBLEM TO BE SOLVED: To provide a simple production method of a primary amine compound unnecessary for complicated procedures and toxic sodium azide or the like. SOLUTION: A production method of a primary amine compound includes a step for reacting a ketone compound and an oxime compound in the presence of alcohol and an acid catalyst. Preferably, the acid catalyst is hydrochloric acid, sulfuric acid, methanesulfonic acid, camphorsulfonic acid, a tosyl acid hydrate, trifluoromethane sulfonic acid or a boron trifluoride diethyl ether complex. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Metal-free Semiconductor Photocatalysis for sp2 C?H Functionalization with Molecular Oxygen

Designing metal-free catalysts for solar energy conversion is a long-standing challenge in semiconductor photoredox catalysis (SPC). With visible-light-responsive hexagonal boron carbon nitride (h-BCN) as a non-metal photocatalyst, this system affords C?H/N?H coupling products with broad substitution tolerance and high efficiency with molecular oxygen as the terminal oxidant. The catalyst exhibits remarkable performance for the selective C?H functionalization of electron-rich arenes to C?N products (yields up to 95 %) and good stability (6 recycles). Both nitrogen heteroarenes and amine salts are competent coupling nucleophiles. Mechanically, the reactive oxygen species are superoxide anion radical (O2?.) and H2O2, which are proved by electron spin resonance (ESR) data, KI-starch, and control experiments. In addition, kinetic isotope effect (KIE) experiments indicate that C?H bond cleavage is not involved in the rate limiting step. This semiconductor-based photoredox system allows for C?H amination free of any metals, ligands, strong oxidants, and additives. It provides a complementary avenue to C?H functionalizations and enables synthetic applications efficiently in a sustainable manner.

Highly selective reduction of nitrobenzenes to azoxybenzenes with a copper catalyst

A convenient protocol for highly selective delivery of azoxybenzenes from reduction of nitrobenzenes was developed by utilizing a copper catalyst. A variety of functional groups and substitution were well tolerated.

Method of preparing arylamine by photo-catalyzing C-H activation with semiconductor

The invention discloses a method of preparing arylamine by photo-catalyzing C-H activation with a semiconductor. The method comprises the following steps of by taking an aromatic compound as a substrate and boron-nitrogen-carbon as a photocatalyst, adding an amino source, a solvent and alkali, performing stirring reaction for 48h under the condition of visible light radiation at room temperature in an oxygen atmosphere, and synthesizing an arylamine compound. The boron-nitrogen-carbon (h-BCN) is a semiconductor polymer photocatalyst which responds to visible light and does not contain metallicelements and has the advantages of low cost, availability, good chemical stability, non toxicity, innocuousness, proper forbidden band width and energy band position and the like. The catalyst is used for synthesizing the arylamine compound, is simple in operation in reaction process, is performed under the visible light, is mild in condition and good in catalytic effect and has the yield, to a target product, reaching 72 percent. The method provided by the invention is simple in technology and low in cost, accords with the actual production needs and has relatively large application potential.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.

Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia

A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.

Transition-metal-free access to primary anilines from boronic acids and a common +NH2 equivalent

Diversely substituted anilines are prepared by treatment of functionalized arylboronic acids with a common, inexpensive source of electrophilic nitrogen (H2N-OSO3H, HSA) under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method. However, even moderately electron-poor substrates are well tolerated under the room temperature conditions. Sterically hindered substrates appear to be equally effective compared to unhindered ones. Highly electron-deficient substrates afford product in very low yields at room temperature, but moderate to good yields are obtained at refluxing temperatures. Our method is also amenable to electrophilic amination of several common boronic acid derivatives (e.g., pinacol esters). We demonstrate that it can be combined with metal-halogen exchange reactions or a variety of directed ortho metalation protocols in a "one-pot" sequence for the synthesis of aromatic amines with unique substitution patterns. DFT studies, in combination with experimental results, suggest that the reaction occurs via base-mediated activation of HSA, followed by 1,2 aryl B-N migration. This mode of activation appears to be critical for the success of the reaction and allows, for the first time, a general, electrophilic amination of boronic acids at ambient temperature.

Silicon analogues of the nonpeptidic GnRH antagonist AG-045572: Syntheses, crystal structure analyses, and pharmacological characterization

AG-045572 (CMPD1, 1a) is a nonpeptidic gonadotropin-releasing hormone (GnRH) antagonist that has been investigated for the treatment of sex hormone-related diseases. In the context of systematic studies on sila-substituted drugs, the silicon analogue disila-AG-045572 (1b) and its derivative 2 were prepared in multi-step syntheses and characterized by elemental analyses (C, H, N), NMR spectroscopic studies (1H, 13C, 29Si), and single-crystal X-ray diffraction. The pharmacological properties of compounds 1a, 1b, and 2 were compared in terms of their in vitro potency at cloned human and rat GnRH receptors. Compounds 1a and 2 were also examined in regard to their pharmacokinetics and in vivo efficacy in both castrated rat (luteinizing hormone (LH) suppression) and intact rat (testosterone suppression) models. The efficacy and pharmacokinetic profiles of 1a and its silicon-containing analogue 2 appear similar, indicating that replacement of the 5,6,7,8-tetrahydronaphthalene ring system by the 1,3-disilaindane skeleton led to retention of efficacy. Therefore, the silicon compound 2 represents a novel drug prototype for the design of potent, orally available GnRH antagonists suitable for once-daily dosing.

PIPERIDYL DERIVATIVES

A compound of the formula (I): wherein R1, R2, R8, R9 and R10 are each as defined in the description, and -X- is -NH or -O-,Y is (II), (III), (IV), etc., and -Z- is bond or (V) in which R3, R4, R5, R6, R7, and R11 are each as defined in the description, or a salt thereof. The object compound of the present invention has pharmacological activities such as Tachykinin antagonism, and is useful for manufacture of a medicament for treating or preventing Tachykinin-mediated diseases.