87814-40-2

Upstream product

• 5049-61-6 2-Aminopyrazine 
• 55919-47-6 ethyl 2-bromo-3-oxo-3-phenylpropionate 
• 98-88-4 benzoyl chloride 
• 10364-94-0 1-benzoylimidazole 
• 100-52-7 benzaldehyde 
• 93-58-3 benzoic acid methyl ester 
• 1864-94-4 phenyl formate 
• 14508-49-7 2-chloropyrazin 
• 55-21-0 benzamide 
• 21251-12-7 N-benzoyl-O-acetylhydroxylamine 
• 201024-81-9 C,N-diphenylnitrone 
• 27955-58-4 2-phenylimidazo<1,2-a>pyrazin-3(7H)-one 

Downstream Products

• 143211-52-3 2-(5-Phenyl-tetrazol-1-yl)-pyrazine 
• 143211-53-4 2-phenyl-[1,2,4]triazolo[1,5-a]pyrazine 

Relevant academic research and scientific papers

Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation

A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.

Design, synthesis and evaluation of N-pyrazinylbenzamides as potential antimycobacterial agents

Three series of N-(pyrazin-2-yl)benzamides were designed as retro-amide analogues of previously published N-phenylpyrazine-2-carboxamides with in vitro antimycobacterial activity. The synthesized retro-amides were evaluated for in vitro growth inhibiting activity against Mycobacterium tuberculosis H37Rv (Mtb), three non-tuberculous mycobacterial strains (M. avium, M. kansasii, M. smegmatis) and selected bacterial and fungal strains of clinical importance. Regarding activity against Mtb, most N-pyrazinylbenzamides (retro-amides) possessed lower or no activity compared to the corresponding N-phenylpyrazine-2-carboxamides with the same substitution pattern. However, the active retro-amides tended to have lower HepG2 cytotoxicity and better selectivity. Derivatives with 5-chloro substitution on the pyrazine ring were generally more active compared to their 6-cloro positional isomers or non-chlorinated analogues. The best antimycobacterial activity against Mtb was found in N-(5-chloropyrazin-2-yl)benzamides with short alkyl (2h: R2 = Me; 2i: R2 = Et) in position 4 of the benzene ring (MIC = 6.25 and 3.13 μg/mL, respectively, with SI > 10). N-(5-Chloropyrazin-2-ylbenzamides with hydroxy substitution (2b: R2 = 2-OH; 2d: R2 = 4-OH) on the benzene ring or their acetylated synthetic precursors possessed the broadest spectrum of activity, being active in all three groups of mycobacterial, bacterial and fungal strains. The substantial differences in in silico calculated properties (hydrogen-bond pattern analysis, molecular electrostatic potential, HOMO and LUMO) can justify the differences in biological activities between N-pyrazinylbenzamides and N-phenylpyrazine-2-carboxamides.

Blue Fluorescence from BF2 Complexes of N,O-Benzamide Ligands: Synthesis, Structure, and Photophysical Properties

Small molecules having intense luminescence properties are required to promote biological and organic material applications. We prepared five types of benzamides having pyridine, pyridazine, pyrazine, and pyrimidine rings and successfully converted them i

Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes

A sustainable procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions has been reported. The transformation has proven to tolerate a wide range of aldehydes and amino heterocycles with different functional groups. Moderate to excellent yields, solvent-free media, operational simplicity and reusability of catalysts are the main highlights. Furthermore, the proposed N-directing dual-catalysis mechanistic pathway was briefly investigated in this report.

Metal-free oxidative amidation of aldehydes with aminopyridines employing aqueous hydrogen peroxide

The first metal free report on the amidation of aldehydes with aminopyridines was accomplished using simple aqueous hydrogen peroxide (aq. H2O2) as the oxidant. No catalysts or additives were needed for this transformation and the reaction proceeded in water, an environmentally benign reaction medium. Green oxidant and reaction conditions, and the ability to construct diverse N-(pyridin-2-yl)benzamide by this elegant method render it a practical alternative for the synthesis of these amides.

Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives

Based on spectroscopic measurements and DFT calculations, fluorescence properties of thiazolo[4,5-b]pyrazine (TPy) derivatives with the phenyl group at the C2 position were studied. TPys were readily prepared from the corresponding amidopyrazines, which have a similar fluorescent core to a bioluminescence light emitter, Cypridina oxyluciferin. It was found that the introduction of electron-donating (methoxy and dimethylamino) groups onto the 2-phenyl moiety of the TPy derivatives, as well as the phenyl and 4-(dimethylamino)phenyl groups at C2 and C6, respectively, increases the fluorescence yield and appearance of solvatochromic character. The mechanism of increasing the fluorescence yield depending on the substituents is discussed. These findings provide useful information on designing new TPy fluorophores. This journal is

Aryl formate as bifunctional reagent: Applications in palladium-catalyzed carbonylative coupling reactions using in situ generated CO

After decades of development, carbonylation reactions have become one of the most powerful tools in modern organic synthesis. However, the requirement of CO gas limits the applications of such reactions. Reported herein is a versatile and practical protocol for carbonylative reactions which rely on the cooperation of phenyl formate and nonaflate, and the generation of CO in situ. This protocol has a high functional-group tolerance and could be applied in carbonylations with C, N, and, O nucleophiles. The corresponding amides, alkynones, furanones, and aryl benzoates were synthesized in good yields. Transformers: A versatile and practical protocol for carbonylation reactions involve the cooperation of phenyl formate and nonaflate with generation of CO in situ. This protocol has a high functional-group tolerance and could be applied in carbonylative couplings with C, N, and O nucleophiles. The corresponding amides, alkynones, furanones, and aryl benzoates were synthesized in good yield.

Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions

A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, resulting in the preparation of amides in-line from haloarenes. This journal is

Copper-catalysed amidation of 2-chloro-pyridines

The simple and inexpensive N,N-dimethylcyclohexane-1,2-diamine/CuI catalytic system provides a versatile, easy and efficient access to an array of N-(2-pyridin-2-yl)-amides from 2-chloro-pyridine derivatives. The Royal Society of Chemistry 2013.

N,N-carbonyldiimidazole-mediated amide coupling: Significant rate enhancement achieved by acid catalysis with imidazole - HCI

Over a series of 10 aromatic amines we show the rate of CDI mediated amidation to be significantly enhanced upon introduction of imidazole·HCI as a proton source for acid catalysis. Our work supports and provides an application for previous investigations into the imidazolium effect, thus increasing the scope of CDI as an amide-coupling reagent with aromatic amines. The influence of the relative pKa of the amines studied on the rate of reaction was also investigated.