112193-05-2

Upstream product

• 7251-61-8 2-methylquinoxaline 
• 100-46-9 benzylamine 
• 95-54-5 1,2-diamino-benzene 
• 1210881-27-8 2-phenethylquinoxaline 
• 100-51-6 benzyl alcohol 
• 6640-55-7 2-methyl-1,2,3,4-tetrahydroquinoxaline 
• 100-52-7 benzaldehyde 
• 91-19-0 2,3-diethynylquinoxaline 
• 6935-29-1 quinoxaline-N-oxide 
• 100-42-5 styrene 
• 758640-21-0 N-Benzylaniline 
• 51608-60-7 phenyl N-tosyl imine 
• 1448-87-9 2-chloroquinoxaline 
• 817165-82-5 2-[(Triphenyl-λ⁵-phosphanylidene)-methyl]-quinoxaline 

Downstream Products

• 106435-53-4 2-chloromethyl-quinoxaline 
• 41242-94-8 2-hydroxymethylquinoxaline 
• 879-65-2 quinoxaline-2-carboxylic acid 

Relevant academic research and scientific papers

Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes with Primary Alcohols

Herein, we present the first catalytic direct olefination of methyl-substituted heteroarenes with primary alcohols through an acceptorless dehydrogenative coupling. The reaction is catalyzed by a complex of the earth-abundant transition metal manganese that is stabilized by a bench-stable NNN pincer ligand derived from 2-hydrazinylpyridine. The reaction is environmentally benign, producing only hydrogen and water as byproducts. A large number of E-disubstituted olefins were selectively obtained with high efficiency.

Palladium-catalyzed C–H alkenylation of quinoxaline N-oxide enabled by a mono-N-protected amino acid

The efficient alkenylation of quinoxaline N-oxide was achieved via Pd-catalyzed C–H activation, using the assistance of a mono-N-protected amino acid. Further deoxygenation of the 2-styrylquinoxaline-N-oxides yielded the corresponding styrylquinoxaline de

Direct alkenylation of 2-substituted azaarenes with carbonyls via C-H bond activation using iron-based metal-organic framework Fe3O(BPDC)3 as an efficient heterogeneous catalyst

A porous crystalline metal-organic framework Fe3O(BPDC)3 was synthesized from the reaction of biphenyl-4,4′-dicarboxylic acid and iron(III) chloride hexahydrate by a solvothermal method in the presence of acetic acid, and was characterized by using a variety of different techniques. The Fe3O(BPDC)3 could be used as an efficient heterogeneous catalyst in the synthesis of 2-alkenylazaarenes using the direct alkenylation of 2-substituted azaarenes with carbonyls via C-H bond activation. The presence of acetic acid as a co-catalyst accelerated the transformation significantly. The Fe3O(BPDC)3 exhibited better performance in this transformation then other MOFs such as Fe3O(BDC)3, Cu2(OBA)2(BPY), Cu2(BDC)2(DABCO), Ni2(BDC)2(DABCO), Zn-MOF-74, and Cu2(NDC)2(DABCO). The Fe3O(BPDC)3 also exhibited higher catalytic activity than that of several homogeneous catalysts such as FeCl2, FeCl3, CuCl2, Zn(OAc)2, Zn(NO3)2, and Ni(OAc)2. The Fe3O(BPDC)3 catalyst could be recovered and reused several times in the synthesis of 2-alkenylazaarenes without a significant degradation in catalytic activity. To the best of our knowledge, 2-alkenylazaarenes was not previously synthesized via the direct alkenylation of 2-substituted azaarenes with carbonyls using heterogeneous catalysts.

Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C-H activation

Herein we present an efficient and regioselective iron-catalyzed methodology for the external oxidant-free functionalization of quinoline-N-oxides. The protocol, based on the use of inexpensive and easily accessible FeSO4, showed broad applicability to a wide range of substrates. An additional green feature of this synthetic methodology is H2O being the only by-product. Experimental and computational investigations provide support to a mechanism based on a facile C-H activation event. The green efficiency of the process has also been carefully assessed using: (i) metrics related to the synthetic process (AE, Yield, 1/SF, MRP and RME); (ii) safety/hazard metrics (SHZI and SHI); and (iii) metrics related to the metal used as the catalyst (Abundance, OEL and ADP). In addition to the many advantages of this protocol related to the green iron catalyst used and the safety/hazard features of the process, an E-factor value of ca. 0.92 (84 to >99% reduction compared to known protocols) evidently confirms the sustainable efficiency of the procedure presented. Practical utility has also been demonstrated by performing the reaction efficiently on a multi-gram scale. This journal is

Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

NH4I-mediated sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinoline for the synthesis of E-2-styrylquinolines

Without any metal catalyst, a simple and efficient method for the synthesis of E-2-styrylquinolines through sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinolines mediated by NH4I under air is successfully developed. The oxidative olefination proceeded through deamination and sp3 C–H bond activation. A plausible mechanism is proposed for the construction of E-2-styrylquinolines.

Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols

A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.

Method for alkenylation of methyl heterocyclic compound

The invention discloses a method for alkenylation of methyl heterocyclic compound, which is a green method for synthesizing an alkenyl heterocyclic compound by carrying out alkenylation reaction on methyl under the condition that the methyl heterocyclic compound and alcohol do not need to participate in a transition metal catalyst. According to the method, alcohol which is cheap, easy to obtain, wide in source, stable and low in toxicity is used as an alkenylation reagent, no transition metal catalyst or ligand is needed, air can be directly used as a convenient, mild and efficient oxidizing agent under the action of common water-soluble inorganic base, and the method is suitable for industrial production. The alkenyl heterocyclic compound is directly synthesized by carrying out a Cenylation reaction with a methyl heterocyclic compound through processes such as oxidative condensation and the like. The method has the advantages of simple reaction conditions, no need of inert gas protection, low requirements on equipment, easiness in operation, water as a byproduct, easiness in removal of water-soluble inorganic base, no metal residue in the product, easiness in purification, suitability for heterocyclic systems such as quinoline, quinoxaline, pyridine, benzothiazole and the like, and wide application range, thereby having certain research significance and potential application prospect.

Nickel(II)-Catalyzed Selective (E)-Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction

An efficient catalytic protocol for the synthesis of selective (E)-olefins by the newly synthesized nickel complexes via greener acceptorless dehydrogenative coupling methodology is presented. Two nickel(II) N, S chelating complexes were structurally characterized with the aid of spectral and single crystal X-ray diffraction methods. Olefination of 2-methylheteroarenes with benzyl alcohols via acceptorless dehydrogenative coupling is achieved by inexpensive nickel(II) catalysts. The present olefination protocol is simple and furnishes the desired 2-alkenylheteroarenes in 35 h and yields in the range of 40–93 %. The dehydrogenative coupling reaction proceeds via the generation of an aldehyde intermediate and produces water and hydrogen as sole by-products. The wide substrate scope of this catalytic reaction covered the synthesis of drug intermediates.

A heterogeneous and recoverable palladium catalyst to access the regioselective C-H alkenylation of quinoline: N -oxides

Herein, we disclose the first C-2-selective C-H alkenylation of quinoline N-oxides catalyzed using a heterogeneous palladium catalyst. The protocol does not require the use of an external oxidant and it is applicable to an ample substrate scope always showing excellent site selectivity. This process is made accessible by the use of a specific 1,2,3-triazolium-tagged heterogeneous polymeric catalytic system. The catalyst can be efficiently recovered and reused with no decrease of its catalytic performance and hot filtration and mercury poisoning tests suggest that its mechanism of action is operatively heterogeneous. In addition, mechanistic studies revealed that C-H activation reaction pathways are operative, setting the stage for the direct synthesis of 2-functionalized quinolines using N-oxide functionality as both a directing group and an oxidant.