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AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles.

Chemical communications (Cambridge, England)

Wu D, Zhang J, Cui J, Zhang W, Liu Y.
PMID: 25089911
Chem Commun (Camb). 2014 Sep 25;50(74):10857-60. doi: 10.1039/c4cc01327a.

A unique method for AgNO2-mediated direct nitration of the quinoxaline tertiary C-H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed. This protocol provides an efficient way to access quinoxaline containing nitroalkanes...

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Wu D, Zhang J, Cui J, et al. AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles. Chem Commun (Camb). 2014;50(74):10857-60doi: 10.1039/c4cc01327a.
Wu, D., Zhang, J., Cui, J., Zhang, W., & Liu, Y. (2014). AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles. Chemical communications (Cambridge, England), 50(74), 10857-60. https://doi.org/10.1039/c4cc01327a
Wu, Degui, et al. "AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles." Chemical communications (Cambridge, England) vol. 50,74 (2014): 10857-60. doi: https://doi.org/10.1039/c4cc01327a
Wu D, Zhang J, Cui J, Zhang W, Liu Y. AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles. Chem Commun (Camb). 2014 Sep 25;50(74):10857-60. doi: 10.1039/c4cc01327a. PMID: 25089911.
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HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer.

Accounts of chemical research

Rozen S.
PMID: 24871453
Acc Chem Res. 2014 Aug 19;47(8):2378-89. doi: 10.1021/ar500107b. Epub 2014 May 28.

The complex HOF·CH3CN is readily obtained by bubbling dilute fluorine into aqueous acetonitrile solution. It does not have to be purified or isolated, and its solution can react as is, after the concentration has been establish by any iodometric...

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Rozen S. HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer. Acc Chem Res. 2014;47(8):2378-89doi: 10.1021/ar500107b.
Rozen, S. (2014). HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer. Accounts of chemical research, 47(8), 2378-89. https://doi.org/10.1021/ar500107b
Rozen, Shlomo. "HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer." Accounts of chemical research vol. 47,8 (2014): 2378-89. doi: https://doi.org/10.1021/ar500107b
Rozen S. HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer. Acc Chem Res. 2014 Aug 19;47(8):2378-89. doi: 10.1021/ar500107b. Epub 2014 May 28. PMID: 24871453.
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Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines.

Organic & biomolecular chemistry

Hung TQ, Hoang do H, Thang NN, Dang TT, Ayub K, Villinger A, Friedrich A, Lochbrunner S, Flechsig GU, Langer P.
PMID: 25001519
Org Biomol Chem. 2014 Aug 28;12(32):6151-66. doi: 10.1039/c4ob00841c. Epub 2014 Jul 08.

A series of indolo[2,3-b]quinoxaline derivatives were efficiently synthesized from 2,3-dibromoquinoxaline by two pathways. A one-pot approach using Pd-catalyzed two-fold C-N coupling and C-H activation reactions gave indolo[2,3-b]quinoxaline derivatives in good yields, but with limited substrate scope. In addition, a...

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Hung TQ, Hoang do H, Thang NN, et al. Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines. Org Biomol Chem. 2014;12(32):6151-66doi: 10.1039/c4ob00841c.
Hung, T. Q., Hoang, d. o. . H., Thang, N. N., Dang, T. T., Ayub, K., Villinger, A., Friedrich, A., Lochbrunner, S., Flechsig, G. U., & Langer, P. (2014). Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines. Organic & biomolecular chemistry, 12(32), 6151-66. https://doi.org/10.1039/c4ob00841c
Hung, Tran Quang, et al. "Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines." Organic & biomolecular chemistry vol. 12,32 (2014): 6151-66. doi: https://doi.org/10.1039/c4ob00841c
Hung TQ, Hoang do H, Thang NN, Dang TT, Ayub K, Villinger A, Friedrich A, Lochbrunner S, Flechsig GU, Langer P. Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines. Org Biomol Chem. 2014 Aug 28;12(32):6151-66. doi: 10.1039/c4ob00841c. Epub 2014 Jul 08. PMID: 25001519.
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FeCl.

Chemical communications (Cambridge, England)

An Z, Zhao L, Wu M, Ni J, Qi Z, Yu G, Yan R.
PMID: 28990598
Chem Commun (Camb). 2017 Oct 19;53(84):11572-11575. doi: 10.1039/c7cc07089f.

A straightforward Fe-catalyzed method for the synthesis of pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclic ethers, which includes functionalization of C(sp

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An Z, Zhao L, Wu M, et al. FeCl. Chem Commun (Camb). 2017;53(84):11572-11575doi: 10.1039/c7cc07089f.
An, Z., Zhao, L., Wu, M., Ni, J., Qi, Z., Yu, G., & Yan, R. (2017). FeCl. Chemical communications (Cambridge, England), 53(84), 11572-11575. https://doi.org/10.1039/c7cc07089f
An, Zhenyu, et al. "FeCl." Chemical communications (Cambridge, England) vol. 53,84 (2017): 11572-11575. doi: https://doi.org/10.1039/c7cc07089f
An Z, Zhao L, Wu M, Ni J, Qi Z, Yu G, Yan R. FeCl. Chem Commun (Camb). 2017 Oct 19;53(84):11572-11575. doi: 10.1039/c7cc07089f. PMID: 28990598.
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Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines.

The Journal of organic chemistry

Jiao YX, Wu LL, Zhu HM, Qin JK, Pan CX, Mo DL, Su GF.
PMID: 28375010
J Org Chem. 2017 Apr 21;82(8):4407-4414. doi: 10.1021/acs.joc.7b00011. Epub 2017 Apr 04.

Diverse functionalized quinoxalines were synthesized in good yields from arylamines and readily available β-keto oximes through condensation and metal-free N-arylation. The reaction was compatible with various functional groups, such as halides, cyano, and esters. A mechanism was proposed based...

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Jiao YX, Wu LL, Zhu HM, et al. Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines. J Org Chem. 2017;82(8):4407-4414doi: 10.1021/acs.joc.7b00011.
Jiao, Y. X., Wu, L. L., Zhu, H. M., Qin, J. K., Pan, C. X., Mo, D. L., & Su, G. F. (2017). Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines. The Journal of organic chemistry, 82(8), 4407-4414. https://doi.org/10.1021/acs.joc.7b00011
Jiao, Yan-Xiao, et al. "Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines." The Journal of organic chemistry vol. 82,8 (2017): 4407-4414. doi: https://doi.org/10.1021/acs.joc.7b00011
Jiao YX, Wu LL, Zhu HM, Qin JK, Pan CX, Mo DL, Su GF. Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines. J Org Chem. 2017 Apr 21;82(8):4407-4414. doi: 10.1021/acs.joc.7b00011. Epub 2017 Apr 04. PMID: 28375010.
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Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles.

The Journal of organic chemistry

Pinho e Melo TM, Lopes CS, Gonsalves AM, Beja AM, Paixão JA, Silva MR, da Veiga LA.
PMID: 11777440
J Org Chem. 2002 Jan 11;67(1):66-71. doi: 10.1021/jo010504v.

Nucleophilic substitution reactions of 2-halo-2H-azirines 1a, 1b, 1d, and 1e with potassium phthalimide and aniline allowed the preparation of new substituted 2H-azirines 2-5. The reactions of 2-bromo-2H-azirine 1a with methylamine led to the synthesis of alpha-diimines 7 and 8....

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Pinho e Melo TM, Lopes CS, Gonsalves AM, et al. Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. J Org Chem. 2002;67(1):66-71doi: 10.1021/jo010504v.
Pinho e Melo, T. M., Lopes, C. S., Gonsalves, A. M., Beja, A. M., Paixão, J. A., Silva, M. R., & da Veiga, L. A. (2002). Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. The Journal of organic chemistry, 67(1), 66-71. https://doi.org/10.1021/jo010504v
Pinho e Melo, Teresa M V D, et al. "Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles." The Journal of organic chemistry vol. 67,1 (2002): 66-71. doi: https://doi.org/10.1021/jo010504v
Pinho e Melo TM, Lopes CS, Gonsalves AM, Beja AM, Paixão JA, Silva MR, da Veiga LA. Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. J Org Chem. 2002 Jan 11;67(1):66-71. doi: 10.1021/jo010504v. PMID: 11777440.
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Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds.

Organic & biomolecular chemistry

Raw SA, Wilfred CD, Taylor RJ.
PMID: 14985820
Org Biomol Chem. 2004 Mar 07;2(5):788-96. doi: 10.1039/b315689c. Epub 2004 Feb 11.

alpha-hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope...

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Raw SA, Wilfred CD, Taylor RJ. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org Biomol Chem. 2004;2(5):788-96doi: 10.1039/b315689c.
Raw, S. A., Wilfred, C. D., & Taylor, R. J. (2004). Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Organic & biomolecular chemistry, 2(5), 788-96. https://doi.org/10.1039/b315689c
Raw, Steven A, et al. "Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds." Organic & biomolecular chemistry vol. 2,5 (2004): 788-96. doi: https://doi.org/10.1039/b315689c
Raw SA, Wilfred CD, Taylor RJ. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org Biomol Chem. 2004 Mar 07;2(5):788-96. doi: 10.1039/b315689c. Epub 2004 Feb 11. PMID: 14985820.
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Platinum-catalyzed formal Markownikoff's hydroamination/hydroarylation cascade of terminal alkynes assisted by tethered hydroxyl groups.

The Journal of organic chemistry

Patil NT, Kavthe RD, Raut VS, Reddy VV.
PMID: 20560573
J Org Chem. 2009 Aug 21;74(16):6315-8. doi: 10.1021/jo901200j.

An efficient method for Markownikoff's hydroamination-hydroarylation of alkynols using PtBr(2) as catalyst has been developed. The platinum-catalyzed reactions of alkynols with amino group containing aromatics were achieved in methanol over a reaction time of 6-24 h and temperature ranging...

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Patil NT, Kavthe RD, Raut VS, et al. Platinum-catalyzed formal Markownikoff's hydroamination/hydroarylation cascade of terminal alkynes assisted by tethered hydroxyl groups. J Org Chem. 2009;74(16):6315-8doi: 10.1021/jo901200j.
Patil, N. T., Kavthe, R. D., Raut, V. S., & Reddy, V. V. (2009). Platinum-catalyzed formal Markownikoff's hydroamination/hydroarylation cascade of terminal alkynes assisted by tethered hydroxyl groups. The Journal of organic chemistry, 74(16), 6315-8. https://doi.org/10.1021/jo901200j
Patil, Nitin T, et al. "Platinum-catalyzed formal Markownikoff's hydroamination/hydroarylation cascade of terminal alkynes assisted by tethered hydroxyl groups." The Journal of organic chemistry vol. 74,16 (2009): 6315-8. doi: https://doi.org/10.1021/jo901200j
Patil NT, Kavthe RD, Raut VS, Reddy VV. Platinum-catalyzed formal Markownikoff's hydroamination/hydroarylation cascade of terminal alkynes assisted by tethered hydroxyl groups. J Org Chem. 2009 Aug 21;74(16):6315-8. doi: 10.1021/jo901200j. PMID: 20560573.
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A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds.

The Journal of organic chemistry

Troian-Gautier L, De Winter J, Gerbaux P, Moucheron C.
PMID: 24069899
J Org Chem. 2013 Nov 01;78(21):11096-101. doi: 10.1021/jo401872e. Epub 2013 Oct 10.

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent...

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Troian-Gautier L, De Winter J, Gerbaux P, et al. A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds. J Org Chem. 2013;78(21):11096-101doi: 10.1021/jo401872e.
Troian-Gautier, L., De Winter, J., Gerbaux, P., & Moucheron, C. (2013). A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds. The Journal of organic chemistry, 78(21), 11096-101. https://doi.org/10.1021/jo401872e
Troian-Gautier, Ludovic, et al. "A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds." The Journal of organic chemistry vol. 78,21 (2013): 11096-101. doi: https://doi.org/10.1021/jo401872e
Troian-Gautier L, De Winter J, Gerbaux P, Moucheron C. A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds. J Org Chem. 2013 Nov 01;78(21):11096-101. doi: 10.1021/jo401872e. Epub 2013 Oct 10. PMID: 24069899.
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Genotoxic risk of quinocetone and its possible mechanism in .

Toxicology research

Wang X, Yang P, Li J, Ihsan A, Liu Q, Cheng G, Tao Y, Liu Z, Yuan Z.
PMID: 30090359
Toxicol Res (Camb). 2015 Nov 25;5(2):446-460. doi: 10.1039/c5tx00341e. eCollection 2016 Mar 01.

Quinoxalines possessing the quinoxaline-1,4-dioxide (QdNOs) basic structure are used for their antibacterial action, although their mechanism of genotoxicity is not clear. After comparing the sensitivity of V79 cells and HepG2 cells to quinocetone (QCT) and other QdNOs, it was...

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Wang X, Yang P, Li J, et al. Genotoxic risk of quinocetone and its possible mechanism in . Toxicol Res (Camb). 2015;5(2):446-460doi: 10.1039/c5tx00341e.
Wang, X., Yang, P., Li, J., Ihsan, A., Liu, Q., Cheng, G., Tao, Y., Liu, Z., & Yuan, Z. (2016). Genotoxic risk of quinocetone and its possible mechanism in . Toxicology research, 5(2), 446-460. https://doi.org/10.1039/c5tx00341e
Wang, Xu, et al. "Genotoxic risk of quinocetone and its possible mechanism in ." Toxicology research vol. 5,2 (2016): 446-460. doi: https://doi.org/10.1039/c5tx00341e
Wang X, Yang P, Li J, Ihsan A, Liu Q, Cheng G, Tao Y, Liu Z, Yuan Z. Genotoxic risk of quinocetone and its possible mechanism in . Toxicol Res (Camb). 2015 Nov 25;5(2):446-460. doi: 10.1039/c5tx00341e. eCollection 2016 Mar 01. PMID: 30090359; PMCID: PMC6062406.
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A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives.

The Journal of organic chemistry

Li J, Zhang J, Yang H, Gao Z, Jiang G.
PMID: 28056510
J Org Chem. 2017 Jan 06;82(1):765-769. doi: 10.1021/acs.joc.6b02501. Epub 2016 Dec 08.

A practical and concise protocol for the efficient preparation of pyrrolo[1,2-a]quinoxalines through a cascade of alcohol oxidation/imine formation/intramolecular cyclization/oxidative dehydrogenation has been established. A series of substituted pyrrolo[1,2-a]quinoxaline derivatives were constructed readily in yields of 53-93% from the cheap...

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Li J, Zhang J, Yang H, et al. A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives. J Org Chem. 2016;82(1):765-769doi: 10.1021/acs.joc.6b02501.
Li, J., Zhang, J., Yang, H., Gao, Z., & Jiang, G. (2017). A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives. The Journal of organic chemistry, 82(1), 765-769. https://doi.org/10.1021/acs.joc.6b02501
Li, Jixing, et al. "A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives." The Journal of organic chemistry vol. 82,1 (2017): 765-769. doi: https://doi.org/10.1021/acs.joc.6b02501
Li J, Zhang J, Yang H, Gao Z, Jiang G. A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives. J Org Chem. 2017 Jan 06;82(1):765-769. doi: 10.1021/acs.joc.6b02501. Epub 2016 Dec 08. PMID: 28056510.
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Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines.

Chemical communications (Cambridge, England)

Yuan Y, Dong WH, Gao XS, Xie XM, Zhang ZG.
PMID: 31528936
Chem Commun (Camb). 2019 Oct 01;55(79):11900-11903. doi: 10.1039/c9cc05655f.

A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed...

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Yuan Y, Dong WH, Gao XS, et al. Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines. Chem Commun (Camb). 2019;55(79):11900-11903doi: 10.1039/c9cc05655f.
Yuan, Y., Dong, W. H., Gao, X. S., Xie, X. M., & Zhang, Z. G. (2019). Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines. Chemical communications (Cambridge, England), 55(79), 11900-11903. https://doi.org/10.1039/c9cc05655f
Yuan, Yao, et al. "Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines." Chemical communications (Cambridge, England) vol. 55,79 (2019): 11900-11903. doi: https://doi.org/10.1039/c9cc05655f
Yuan Y, Dong WH, Gao XS, Xie XM, Zhang ZG. Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: synthesis of cyclopenta[b]quinoxalines. Chem Commun (Camb). 2019 Oct 01;55(79):11900-11903. doi: 10.1039/c9cc05655f. PMID: 31528936.
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Showing 1 to 12 of 136 entries