An efficient synthetic route of quinoxalines from diols catalyzed by [RuCl2(p-cymene)]2/1,4-bis(diphenylphosphino)butane

Journal of Organometallic Chemistry - Tập 993 - Trang 122713 - 2023
Peng Zeng1, Xinming Li2, Lin Li2, Cuien Liang1, Jing Zhang2, Tianyou Peng2
1School of Food and Pharmaceutical Engineering, Zhaoqing University, Zhaoqing, 526061, PR China
2College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, PR China

Tài liệu tham khảo

Zaki, 2021, Evaluation of synthetic 2,4-disubstituted-benzo[g] quinoxaline derivatives as potential anticancer agents, Pharmaceuticals, 14, 853, 10.3390/ph14090853 Fayed, 2021, Design, synthesis, antiproliferative evaluation, and molecular docking study of new quinoxaline derivatives as apoptotic inducers and EGFR inhibitors, J. Mol. Struct., 1236, 10.1016/j.molstruc.2021.130317 Ahmed, 2022, Novel quinoxaline derivatives as dual EGFR and COX-2 inhibitors: synthesis, molecular docking and biological evaluation as potential anticancer and anti-inflammatory agents, RSC Adv., 12, 25204, 10.1039/D2RA04498F Lindsley, 2005, Allosteric Akt (PKB) inhibitors: discovery and SAR of isozyme selective inhibitors, Bioorg. Med. Chem. Lett., 15, 761, 10.1016/j.bmcl.2004.11.011 Kim, 2004, Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues, Bioorg. Med. Chem. Lett., 14, 541, 10.1016/j.bmcl.2003.09.086 Wang, 2022, Color-tunable supramolecular luminescent materials, Adv. Mater., 34 Al-Marhabi, 2023, D-D-π-A-π-A-based quinoxaline dyes incorporating phenothiazine, phenoxazine and carbazole as electron donors: synthesis, photophysical, electrochemical, and computational investigation, J. Photochem. Photobiol. A Chem., 436, 10.1016/j.jphotochem.2022.114389 Yang, 2020, A high-throughput screening method for determining the optimized synthesis conditions of quinoxaline derivatives using microdroplet reaction, Front. Chem., 8, 00789, 10.3389/fchem.2020.00789 Rozzi, 2022, Tuning the conformational flexibility of quinoxaline cavitands for complexation at the gas–solid interface, Chem. Commun., 58, 7554, 10.1039/D2CC02710K Ayaz, 2014, Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction, Tetrahedron Lett., 55, 3406, 10.1016/j.tetlet.2014.04.013 Das, 2018, Phosphine free Mn-complex catalysed dehydrogenative C–C and C–heteroatom bond formation: a sustainable approach to synthesize quinoxaline, pyrazine, benzothiazole and quinoline derivatives, Chem. Commun., 54, 10582, 10.1039/C8CC05877F Jeena, 2014, An environmentally friendly, cost effective synthesis of quinoxalines: the influence of microwave reaction conditions, Tetrahedron Lett., 55, 642, 10.1016/j.tetlet.2013.11.100 Shee, 2020, Nickel-catalyzed direct synthesis of quinoxalines from 2-nitroanilines and vicinal diols: identifying nature of the active catalyst, J. Org. Chem., 85, 2775, 10.1021/acs.joc.9b03104 Bains, 2020, Homogeneous nickel-catalyzed sustainable synthesis of quinoline and quinoxaline under aerobic conditions, J. Org. Chem., 85, 14971, 10.1021/acs.joc.0c01819 Daw, 2018, Synthesis of pyrazines and quinoxalines via acceptorless dehydrogenative coupling routes catalyzed by manganese pincer complexes, ACS Catal., 8, 7734, 10.1021/acscatal.8b02208 Khatoon, 2021, Novel synthetic routes to prepare biologically active quinoxalines and their derivatives: a synthetic review for the last two decades, Molecules, 26, 1055, 10.3390/molecules26041055 Guo, 2018, C-N bond formation catalyzed by ruthenium nanoparticles supported on N-doped carbon via acceptorless dehydrogenation to secondary amines, imines, benzimidazoles and quinoxalines, ChemCatChem, 10, 5627, 10.1002/cctc.201801525 Gao, 2017, One-pot aqueous-phase synthesis of quinoxalines through oxidative cyclization of deoxybenzoins with 1,2-phenylenediamines catalyzed by a zwtterionic Cu(II)/calix[4]arene complex, Chin. Chem. Lett., 28, 1087, 10.1016/j.cclet.2016.12.035 Butters, 2006, Critical assessment of pharmaceutical processesa rationale for changing the synthetic route, Chem. Rev., 106, 3002, 10.1021/cr050982w Wang, 2018, Transfer hydrogenation of aldehydes and ketones with isopropanol under neutral conditions catalyzed by a metal-ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(H2O)], J. Org. Chem., 83, 2274, 10.1021/acs.joc.7b03174 Kawahara, 2012, Dehydrogenative oxidation of alcohols in aqueous media using water-soluble and reusable Cp*Ir catalysts bearing a functional bipyridine ligand, J. Am. Chem. Soc., 134, 3643, 10.1021/ja210857z Zhang, 2011, Electron-rich PNP- and PNN-type Ruthenium(II) hydrido borohydride pincer complexes. Synthesis, structure, and catalytic dehydrogenation of alcohols and hydrogenation of esters, Organometallics, 30, 5716, 10.1021/om200595m Dobereiner, 2010, Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis, Chem. Rev., 110, 681, 10.1021/cr900202j Gusev, 2016, Dehydrogenative coupling of ethanol and ester hydrogenation catalyzed by pincer-type YNP complexes, ACS Catal., 6, 6967, 10.1021/acscatal.6b02324 Zhang, 2013, Cobalt-catalyzed acceptorless alcohol dehydrogenation: synthesis of imines from alcohols and amines, Org. Lett., 15, 650, 10.1021/ol303479f Hille, 2017, Synthesis of meta-functionalized pyridines by selective dehydrogenative heterocondensation of β- and γ-amino alcohols, Angew. Chem. Int. Ed., 56, 371, 10.1002/anie.201610071 Kallmeier, 2017, Manganese-catalyzed sustainable synthesis of pyrroles from alcohols and amino alcohols, Angew. Chem. Int. Ed., 56, 7261, 10.1002/anie.201702543 Mastalir, 2016, Sustainable synthesis of quinolines and pyrimidines catalyzed by manganese PNP pincer complexes, J. Am. Chem. Soc., 138, 15543, 10.1021/jacs.6b10433 Xie, 2015, Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a ruthenium-catalyzed hydrogen transfer strategy, Green Chem., 17, 279, 10.1039/C4GC01316F Hille, 2014, The synthesis of benzimidazoles and quinoxalines from aromatic diamines and alcohols by iridium-catalyzed acceptorless dehydrogenative alkylation, Chem. Eur. J., 20, 5569, 10.1002/chem.201400400 Shee, 2018, Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives, Chem. Commun., 54, 6883, 10.1039/C8CC02366B Mondal, 2020, Manganese(I)-catalyzed sustainable synthesis of quinoxaline and quinazoline derivatives with the liberation of dihydrogen, J. Org. Chem., 85, 7181, 10.1021/acs.joc.0c00561 Bera, 2019, Nickel-catalysed dehydrogenative coupling of aromatic diamines with alcohols: selective synthesis of substituted benzimidazoles and quinoxalines, Chem. Commun., 55, 5958, 10.1039/C9CC02319D Yang, 2019, Nickel-catalyzed borrowing hydrogen annulations: access to diversified N-heterocycles, Chem. Commun., 55, 7844, 10.1039/C9CC03975A Dai, 2017, Ni(II)-N′NN′ pincer complexes catalyzed dehydrogenation of primary alcohols to carboxylic acids and H2 accompanied by alcohol etherification, Catal. Sci. Technol., 7, 2506, 10.1039/C7CY00432J Dai, 2017, Ru(II) complexes bearing 2,6-bis(benzimidazole-2-yl)pyridine ligands: a new class of catalysts for efficient dehydrogenation of primary alcohols to carboxylic acids and H2 in the alcohol/CsOH system, J. Organomet. Chem., 830, 11, 10.1016/j.jorganchem.2016.11.038 Dai, 2017, New Ru(II) N′NN′-type pincer complexes: synthesis, characterization and the catalytic hydrogenation of CO2 or bicarbonates to formate salts, New J. Chem., 41, 3055, 10.1039/C6NJ03855G Luo, 2017, Oxidant-free synthesis of benzimidazoles from alcohols and aromatic diamines catalysed by new Ru(II)-PNS(O) pincer complexes, Daltron Trans., 46, 15012, 10.1039/C7DT02584J Li, 2018, Air-stable ruthenium(II)-NNN pincer complexes for the efficient coupling of aromatic diamines and alcohols to 1H-benzo[d]imidazoles with the liberation of H2, ChemCatChem, 10, 1607, 10.1002/cctc.201800017 Tang, 2015, Ruthenium(II) η6-arene complexes containing a dinucleating ligand based on 1,8-naphthyridine, J. Organomet. Chem., 775, 94, 10.1016/j.jorganchem.2014.10.028 Leval, 2020, Formic acid dehydrogenation by a cyclometalated κ3-CNN Ruthenium complex, Eur. J. Inorg. Chem., 14, 1293, 10.1002/ejic.202000068 Higuera-Padilla, 2017, Synthesis of the [(η6-p-cymene)Ru(dppb)Cl]PF6 complex and catalytic activity in the transfer hydrogenation of ketones, J. Coord. Chem., 70, 3541, 10.1080/00958972.2017.1390226 Zhang, 2004, Electron-rich, bulky Ruthenium PNP-type complexes. Acceptorless catalytic alcohol dehydrogenation, Organometallics, 23, 4026, 10.1021/om049716j Pierantozzi, 1980, Photoinduced elimination of molecular hydrogen from [MoH4(diphos)2] and [MoH4(PPh2Me)4], Inorg. Chem., 19, 1821, 10.1021/ic50208a083 Zhang, 2015, Facile conversion of alcohols into esters and dihydrogen catalyzed by new ruthenium complexes, J. Am. Chem. Soc., 127, 10840, 10.1021/ja052862b Zhang, 2007, Electron-rich, bulky PNN-type ruthenium complexes: synthesis, characterization and catalysis of alcohol dehydrogenation, Dalton Trans., 1, 107, 10.1039/B613438F Wang, 2018, Acceptorless dehydrogenation of N-heterocycles and secondary alcohols by Ru(II)-NNC complexes bearing a pyrazoyl-indolyl-pyridine ligand, Organometallics, 37, 584, 10.1021/acs.organomet.7b00902 Fujita, 2017, Reversible interconversion between 2,5-dimethylpyrazine and 2,5-dimethylpiperazine by Iridium-catalyzed hydrogenation/dehydrogenation for efficient hydrogen storage, Angew. Chem. Int. Ed., 56, 10886, 10.1002/anie.201705452 Xu, 2015, Acceptorless, reversible dehydrogenation and hydrogenation of N-heterocycles with a cobalt pincer catalyst, ACS Catal., 5, 6350, 10.1021/acscatal.5b02002 Marichev, 2016, Ruthenium-catalyzed amination of secondary alcohols using borrowing hydrogen methodology, ACS Catal., 6, 2205, 10.1021/acscatal.6b00175 Dang, 2015, Efficient ruthenium-catalyzed n-methylation of amines using methanol, ACS Catal., 5, 4082, 10.1021/acscatal.5b00606 Guo, 2019, Phosphine ligand-free ruthenium complexes as efficient catalysts for the synthesis of quinolines and pyridines by acceptorless dehydrogenative coupling reactions, ChemCatChem, 11, 2500, 10.1002/cctc.201900435 Ventura-Espinsa, 2016, Catalytic hydrogen production by ruthenium complexes from the conversion of primary amines to nitriles: potential application as a liquid organic hydrogen carrier, Chem. Eur. J., 22, 17758, 10.1002/chem.201603423 Sabater, 2014, Catalyst enhancement and recyclability by immobilization of metal complexes onto graphene surface by noncovalent interactions, ACS Catal., 4, 2038, 10.1021/cs5003959 Feng, 2017, Ligand-free RuCl3-catalyzed alkylation of methylazaarenes with alcohols, J. Org. Chem., 82, 4113, 10.1021/acs.joc.6b03095 Tan, 2017, Acceptorless dehydrogenation of alcohols catalyzed by CuI N-heterocycle thiolate complexes, ChemCatChem, 9, 1113, 10.1002/cctc.201601459 Tan, 2018, Ligand-controlled copper(I)-catalyzed cross-coupling of secondary and primary alcohols to α-alkylated ketones, pyridines, and quinolines, Org. Lett., 20, 608, 10.1021/acs.orglett.7b03726 Fox, 2009, A simple synthesis of trans-RuCl(Ctriple bondCR)(dppe)2 complexes and representative molecular structures, J. Organomet. Chem., 694, 2350, 10.1016/j.jorganchem.2009.03.033 Bennett, 1982, (η6-Hexamethylbenzene)Ruthenium complexes, Inorg. Synth., 21, 74, 10.1002/9780470132524.ch16 Dwivedi, 2011, Synthesis, physicochemical and optical characterization of novel fluorescing complex: o-Phenylenediamine-benzoin, J. Fluoresc., 21, 1255, 10.1007/s10895-010-0808-9 Urban, 2011, Ligand-controlled highly regioselective and asymmetric hydrogenation of quinoxalines catalyzed by ruthenium N-heterocyclic carbene complexes, Angew. Chem. Int. Ed., 50, 3803, 10.1002/anie.201100008 Ji, 2017, Naked” iridium(IV) oxide nanoparticles as expedient and robust catalysts for hydrogenation of nitrogen heterocycles: remarkable vicinal substitution effect and recyclability, Adv. Synth. Catal., 359, 933, 10.1002/adsc.201601370 Tak, 2017, Asymmetric catalytic syntheses of pharmaceutically important β-amino-α-hydroxyl esters by enantioselective aminolysis of methyl phenylglycidate, ChemCatChem, 9, 322, 10.1002/cctc.201601208 Garapati, 2018, Oxazolium salts as organocatalysts for the umpolung of aldehydes, Org. Lett., 20, 6372, 10.1021/acs.orglett.8b02636