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Transition metal-catalyzed cross-coupling reactions represent one of the most powerful tools in modern organic chemistry. Due to the relevance of nitrogen heterocyclic compounds for many areas, the development of new and effective methods to afford coupled products from these reagents has become very attractive for organic synthesis. Quinoxaline derivatives encompass one of the most privileged classes of heterocycles, being part of several biologically and technologically relevant compounds. Cross-coupling reactions involving the building block 2,3-dichloroquinoxaline (DCQX) emerge as a promising approach from several synthetic approaches reported for the synthesis of quinoxaline derivatives. The present article consists of a literature review regarding the substrate DCQX as a partner for C-C and C-N cross-coupling reactions. Examples of classical Suzuki-Miyaura, Heck and Sonogashira cross-coupling reactions are presented, as well as other synthetic transformations that lead to the formation of fused polycyclic compounds through heterocyclization processes. Some mechanistic insights are also presented. Notably, most of the publications addressing the subject presented herein are from the last decade, and several of the synthesized compounds are relevant due to their applications in many fields. These features emphasize the relevance of DCQX as a substrate for cross-coupling reactions for organic synthesis.

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Formula: C8H4Cl2N2, New Advances in Chemical Research in 2021. Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.2213-63-0, Name is 2,3-Dichloroquinoxaline, molecular formula is C8H4Cl2N2. In a article,once mentioned of 2213-63-0

The macrocyclic Schiff bases 20-25 were prepared by cyclocondensation of the bis aldehydes 12-15 with the appropriate diaminoalkanes 17-19. Reduction of the latter with NaBH4 afforded the corresponding azacrown ethers 27-30. Heating of the aldehydes 12-16 in refluxing acetic acid afforded the corresponding 2,3-bis(benzofuranyl)quinoxalines 33-37. Nucleophilic reaction of the bis phenols 45-48, 54, 56, 57 with the appropriate dihalo compounds 1, 38 afforded the corresponding macrocyclic diamides 49-52 and 1,omega- bis[quinoxalino(2,3-b)benzoxazepino-13-on-yl]alkanes 60, 61, respectively. (C) 2000 Elsevier Science Ltd.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1324 | ChemSpider

 

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Heating with bromotrimethylsilane converts 2-chloropyridine into 2-bromopyridine and 2-chloro-6-methylpyridine into 2-bromo-6-methylpyridine. Both 2-chloropyridines and 2-bromopyridines give the corresponding iodo compound when treated with in situ generated iodotrimethylsilane. Although 3- and 4-chloropyridine are completely inert, 2,4-dichloropyridine undergoes the halogen/halogen exchange simultaneously at the 2- and 4-position. Halogen displacement takes place exclusively at the 2-position with 2,3-dichloropyridine and 2,5-dichloropyridine. In agreement with the intermediacy of N-trimethylsilylpyridinium salts as a prerequisite for the occurrence of halogen exchange, neither 2-fluoropyridine and 2-fluoro-6-methylpyridine nor any 2,6-dihalopyridine reacts. Finally, bromine/chlorine and iodine/chlorine substitution can also be accomplished with 2-or 4-chloroquinoline, 1-chloroisoquinoline, 2-chloropyrimidine, chloropyrazine and 2,3-dichloroquinoxaline as substrates. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

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Velcrands are a specific class of cavitands whose complementary surfaces induce self-dimerization. The insertion of a velcrand as physical cross-linking unit into a polymer is reported. To this purpose, the velcrand was functionalized at the lower rim with an isocyanate group. The functional velcrand was reacted with poly (ethylene-co-(2-hydroxethylmethacrylate)) (PE-HEMA), a polymer equipped with free hydroxyl groups suitable for reaction with the isocyanate group. The obtained functionalized polymer was characterized by nuclear magnetic resonance (NMR), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR), proving the introduction of velcraplexes in the polymer. Films with varying amounts of velcrands were obtained by solution casting and slow evaporation, testifying the processability of the functionalized polymers. The obtained films were used to measure the oxygen barrier properties of the functionalized material.

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A new series of 1-N-thiocarboxamide-3-phenyl-2-pyrazolines 1-6 was synthesized by cyclization of different Mannich bases with unsubstituted thiosemicarbazide. The reaction of cyclized pyrazoline derivatives 1-6 with 2,3-dichloroquinoxaline afforded the title compounds 7-12. The structures of the new compounds were confirmed by elemental analyses as well as 1H, 13C NMR, IR and electronic spectral data. The HM1:IMSS strain of Entamoeba histolytica parasite was cultured in vitro and the sensitivity of the parasite to the synthesized compounds was evaluated using the microdilution method. Among all the pyrazoline derivatives 1-6, none was found to be a better inhibitor as compared to the reference drug, metronidazole. The quinoxaline derivatives, 9, 11 and 12 were found to be potent inhibitors of E. histolytica.

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A series of 1,3-disubstituted pyrrolo[2,3-b]quinoxalines has been designed for the potential inhibition of PDE4 without inhibiting luciferase. A ligand/PTC (phase transfer catalyst) free intramolecular Heck cyclization strategy was used to prepare these compounds, some of which showed significant inhibition of PDE4B (IC50 ? 5-14 muM) and growth inhibition of oral cancer cells (CAL 27) but not inhibition of luciferase in vitro. They also showed acceptable safety profiles but no apoptosis in zebrafish embryos.

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Product Details of 2213-63-0, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 2213-63-0, Name is 2,3-Dichloroquinoxaline, molecular formula is C8H4Cl2N2. In a article,once mentioned of 2213-63-0

Triphenylphosphine reacts with naphthoquinone diazide to form almost quantitatively the phosphorane of a unique 2-amino-l,2,3-triazole derivative. This compound undergoes an aza-Wittig reaction with aldehydes and is readily hydrolyzed to the free 2-amino-1,2,3-triazole. The free amine reacts normally with acids and aldehydes. The 2-amino-l,2,3-triazole system is stable and high melting, and most derivatives give the parent ion as the largest peak in the mass spectrum. The compounds absorb at 300-350 nm with a strong emission in the range 500-700 nm, depending upon the substituents. Cyclic voltammetry shows one reversible, single-electron reduction wave.

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We report synthesis, X-ray crystal structure, conformational behaviour, and complexation properties of cavitand (1).

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The condensation of 2,3-dichloroquinoxaline with 2-mercaptopyridines and 2-mercaptoquinolines gave the corresponding derivatives of new heterocyclic systems, viz., azino<1',2':3,2>thiazolo<4,5-b>quinoxalinium salts, which can be used for the synthesis of cyanine dyes.

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Related Products of 2213-63-0, New research progress on 2213-63-0 in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 2213-63-0, Name is 2,3-Dichloroquinoxaline, molecular formula is C8H4Cl2N2. In a Article,once mentioned of 2213-63-0

A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

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Quinoxaline – Wikipedia,
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