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Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives.

Chemical communications (Cambridge, England)

Shee S, Ganguli K, Jana K, Kundu S.
PMID: 29790492
Chem Commun (Camb). 2018 Jun 19;54(50):6883-6886. doi: 10.1039/c8cc02366b.

A new phosphine-free Co(ii) complex-catalyzed synthesis of various quinoxalines via dehydrogenative coupling of vicinal diols with both o-phenylenediamines and 2-nitroanilines is reported. This complex was also effective for the synthesis of quinolines. The practical aspect of this catalytic system...

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Shee S, Ganguli K, Jana K, et al. Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives. Chem Commun (Camb). 2018;54(50):6883-6886doi: 10.1039/c8cc02366b.
Shee, S., Ganguli, K., Jana, K., & Kundu, S. (2018). Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives. Chemical communications (Cambridge, England), 54(50), 6883-6886. https://doi.org/10.1039/c8cc02366b
Shee, Sujan, et al. "Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives." Chemical communications (Cambridge, England) vol. 54,50 (2018): 6883-6886. doi: https://doi.org/10.1039/c8cc02366b
Shee S, Ganguli K, Jana K, Kundu S. Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives. Chem Commun (Camb). 2018 Jun 19;54(50):6883-6886. doi: 10.1039/c8cc02366b. PMID: 29790492.
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Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions.

Organic & biomolecular chemistry

Nagarajaiah H, Mishra AK, Moorthy JN.
PMID: 27072599
Org Biomol Chem. 2016 Apr 26;14(17):4129-35. doi: 10.1039/c6ob00351f.

α-Chloroketones - obtained by the atom-economical chlorination of ketones with trichloroisocyanuric acid (TCCA) in the presence of p-TSA under ball-milling conditions - were set up for a sequential base-mediated condensation reaction with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde to afford 2-aminothiazoles,...

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Nagarajaiah H, Mishra AK, Moorthy JN. Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions. Org Biomol Chem. 2016;14(17):4129-35doi: 10.1039/c6ob00351f.
Nagarajaiah, H., Mishra, A. K., & Moorthy, J. N. (2016). Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions. Organic & biomolecular chemistry, 14(17), 4129-35. https://doi.org/10.1039/c6ob00351f
Nagarajaiah, Honnappa, et al. "Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions." Organic & biomolecular chemistry vol. 14,17 (2016): 4129-35. doi: https://doi.org/10.1039/c6ob00351f
Nagarajaiah H, Mishra AK, Moorthy JN. Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions. Org Biomol Chem. 2016 Apr 26;14(17):4129-35. doi: 10.1039/c6ob00351f. PMID: 27072599.
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Rh-Catalyzed tandem C-C/C-N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts.

Organic & biomolecular chemistry

Talukdar K, Roy S, Bag R, Punniyamurthy T.
PMID: 30702737
Org Biomol Chem. 2019 Feb 20;17(8):2148-2152. doi: 10.1039/c8ob03103g.

An efficient Rh-catalyzed oxidative C-H activation/annulation of 2-arylquinoxalines with internal alkynes is described using Cu(OAc)2·H2O and AgBF4 to afford a diverse variety of substituted quarternary ammonium salts at room temperature. The mechanism of the protocol is established on the...

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Talukdar K, Roy S, Bag R, et al. Rh-Catalyzed tandem C-C/C-N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts. Org Biomol Chem. 2019;17(8):2148-2152doi: 10.1039/c8ob03103g.
Talukdar, K., Roy, S., Bag, R., & Punniyamurthy, T. (2019). Rh-Catalyzed tandem C-C/C-N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts. Organic & biomolecular chemistry, 17(8), 2148-2152. https://doi.org/10.1039/c8ob03103g
Talukdar, Kangkan, et al. "Rh-Catalyzed tandem C-C/C-N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts." Organic & biomolecular chemistry vol. 17,8 (2019): 2148-2152. doi: https://doi.org/10.1039/c8ob03103g
Talukdar K, Roy S, Bag R, Punniyamurthy T. Rh-Catalyzed tandem C-C/C-N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts. Org Biomol Chem. 2019 Feb 20;17(8):2148-2152. doi: 10.1039/c8ob03103g. PMID: 30702737.
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5,12-Diacetyl-5,12-dihydroquinoxalino[2,3-b]quinoxalines: Solid-State Fluorescence, AIE Properties, and Orbital Switching by Substituent Effect.

Chemistry, an Asian journal

Miura Y, Yoshioka N.
PMID: 29732740
Chem Asian J. 2018 Jul 04;13(13):1683-1687. doi: 10.1002/asia.201800502. Epub 2018 Jun 19.

The compound 5,12-diacetyl-5,12-dihydroquinoxalino[2,3-b]quinoxaline 1 a and its derivatives were prepared, and their solid- and solution-state spectroscopic properties were studied; 1 a shows stronger fluorescence in solution than in the solid state due to aggregation caused by self-quenching. Phenyl- or...

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Miura Y, Yoshioka N. 5,12-Diacetyl-5,12-dihydroquinoxalino[2,3-b]quinoxalines: Solid-State Fluorescence, AIE Properties, and Orbital Switching by Substituent Effect. Chem Asian J. 2018;13(13):1683-1687doi: 10.1002/asia.201800502.
Miura, Y., & Yoshioka, N. (2018). 5,12-Diacetyl-5,12-dihydroquinoxalino[2,3-b]quinoxalines: Solid-State Fluorescence, AIE Properties, and Orbital Switching by Substituent Effect. Chemistry, an Asian journal, 13(13), 1683-1687. https://doi.org/10.1002/asia.201800502
Miura, Youhei, and Yoshioka, Naoki. "5,12-Diacetyl-5,12-dihydroquinoxalino[2,3-b]quinoxalines: Solid-State Fluorescence, AIE Properties, and Orbital Switching by Substituent Effect." Chemistry, an Asian journal vol. 13,13 (2018): 1683-1687. doi: https://doi.org/10.1002/asia.201800502
Miura Y, Yoshioka N. 5,12-Diacetyl-5,12-dihydroquinoxalino[2,3-b]quinoxalines: Solid-State Fluorescence, AIE Properties, and Orbital Switching by Substituent Effect. Chem Asian J. 2018 Jul 04;13(13):1683-1687. doi: 10.1002/asia.201800502. Epub 2018 Jun 19. PMID: 29732740.
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Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More.

Organic letters

Mastalir M, Glatz M, Pittenauer E, Allmaier G, Kirchner K.
PMID: 30694683
Org Lett. 2019 Feb 15;21(4):1116-1120. doi: 10.1021/acs.orglett.9b00034. Epub 2019 Jan 29.

An efficient synthesis of quinolines, pyrimidines, quinoxalines, pyrroles, and aminomethylated aromatic compounds catalyzed by a well-defined Re(I) PNP pincer complex is described. All reactions proceed with liberation of dihydrogen and elimination of water. Under optimized reaction conditions a wide...

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Mastalir M, Glatz M, Pittenauer E, et al. Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More. Org Lett. 2019;21(4):1116-1120doi: 10.1021/acs.orglett.9b00034.
Mastalir, M., Glatz, M., Pittenauer, E., Allmaier, G., & Kirchner, K. (2019). Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More. Organic letters, 21(4), 1116-1120. https://doi.org/10.1021/acs.orglett.9b00034
Mastalir, Matthias, et al. "Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More." Organic letters vol. 21,4 (2019): 1116-1120. doi: https://doi.org/10.1021/acs.orglett.9b00034
Mastalir M, Glatz M, Pittenauer E, Allmaier G, Kirchner K. Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More. Org Lett. 2019 Feb 15;21(4):1116-1120. doi: 10.1021/acs.orglett.9b00034. Epub 2019 Jan 29. PMID: 30694683.
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Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines.

Organic letters

Ma H, Li D, Yu W.
PMID: 26863185
Org Lett. 2016 Feb 19;18(4):868-71. doi: 10.1021/acs.orglett.6b00148. Epub 2016 Feb 10.

A new method was developed for the synthesis of quinoxalines. This method employs N-arylenamines and TMSN3 as the starting materials and implements two oxidative C-N bond-forming processes in a tandem pattern by using (diacetoxyiodo)benzene as the common oxidant. The...

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Ma H, Li D, Yu W. Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines. Org Lett. 2016;18(4):868-71doi: 10.1021/acs.orglett.6b00148.
Ma, H., Li, D., & Yu, W. (2016). Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines. Organic letters, 18(4), 868-71. https://doi.org/10.1021/acs.orglett.6b00148
Ma, Haichao, et al. "Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines." Organic letters vol. 18,4 (2016): 868-71. doi: https://doi.org/10.1021/acs.orglett.6b00148
Ma H, Li D, Yu W. Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines. Org Lett. 2016 Feb 19;18(4):868-71. doi: 10.1021/acs.orglett.6b00148. Epub 2016 Feb 10. PMID: 26863185.
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Unusual multi-step sequential Au(III)/Au(II) processes of gold(III) quinoxalinoporphyrins in acidic non-aqueous media.

Inorganic chemistry

Ou Z, Zhu W, Fang Y, Sintic PJ, Khoury T, Crossley MJ, Kadish KM.
PMID: 22070403
Inorg Chem. 2011 Dec 19;50(24):12802-9. doi: 10.1021/ic2019567. Epub 2011 Nov 09.

The electrochemistry of gold(III) mono- and bis-quinoxalinoporphyrins was examined in CH(2)Cl(2) or PhCN containing 0.1 M tetra-n-butylammonium perchlorate (TBAP) before and after the addition of trifluoroacetic acid to solution. The investigated porphyrins are represented as Au(PQ)PF(6) and Au(QPQ)PF(6), where...

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Ou Z, Zhu W, Fang Y, et al. Unusual multi-step sequential Au(III)/Au(II) processes of gold(III) quinoxalinoporphyrins in acidic non-aqueous media. Inorg Chem. 2011;50(24):12802-9doi: 10.1021/ic2019567.
Ou, Z., Zhu, W., Fang, Y., Sintic, P. J., Khoury, T., Crossley, M. J., & Kadish, K. M. (2011). Unusual multi-step sequential Au(III)/Au(II) processes of gold(III) quinoxalinoporphyrins in acidic non-aqueous media. Inorganic chemistry, 50(24), 12802-9. https://doi.org/10.1021/ic2019567
Ou, Zhongping, et al. "Unusual multi-step sequential Au(III)/Au(II) processes of gold(III) quinoxalinoporphyrins in acidic non-aqueous media." Inorganic chemistry vol. 50,24 (2011): 12802-9. doi: https://doi.org/10.1021/ic2019567
Ou Z, Zhu W, Fang Y, Sintic PJ, Khoury T, Crossley MJ, Kadish KM. Unusual multi-step sequential Au(III)/Au(II) processes of gold(III) quinoxalinoporphyrins in acidic non-aqueous media. Inorg Chem. 2011 Dec 19;50(24):12802-9. doi: 10.1021/ic2019567. Epub 2011 Nov 09. PMID: 22070403.
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Iridium(III) complexes with orthometalated quinoxaline ligands: subtle tuning of emission to the saturated red color.

Inorganic chemistry

Hwang FM, Chen HY, Chen PS, Liu CS, Chi Y, Shu CF, Wu FI, Chou PT, Peng SM, Lee GH.
PMID: 15732974
Inorg Chem. 2005 Mar 07;44(5):1344-53. doi: 10.1021/ic0489443.

Rational design and syntheses of four iridium complexes (1-4) bearing two substituted quinoxalines and an additional 5-(2-pyridyl) pyrazolate or triazolate as the third coordinating ligand are reported. Single-crystal X-ray diffraction studies of 1 reveal a distorted octahedral geometry, in...

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Hwang FM, Chen HY, Chen PS, et al. Iridium(III) complexes with orthometalated quinoxaline ligands: subtle tuning of emission to the saturated red color. Inorg Chem. 2005;44(5):1344-53doi: 10.1021/ic0489443.
Hwang, F. M., Chen, H. Y., Chen, P. S., Liu, C. S., Chi, Y., Shu, C. F., Wu, F. I., Chou, P. T., Peng, S. M., & Lee, G. H. (2005). Iridium(III) complexes with orthometalated quinoxaline ligands: subtle tuning of emission to the saturated red color. Inorganic chemistry, 44(5), 1344-53. https://doi.org/10.1021/ic0489443
Hwang, Fu-Ming, et al. "Iridium(III) complexes with orthometalated quinoxaline ligands: subtle tuning of emission to the saturated red color." Inorganic chemistry vol. 44,5 (2005): 1344-53. doi: https://doi.org/10.1021/ic0489443
Hwang FM, Chen HY, Chen PS, Liu CS, Chi Y, Shu CF, Wu FI, Chou PT, Peng SM, Lee GH. Iridium(III) complexes with orthometalated quinoxaline ligands: subtle tuning of emission to the saturated red color. Inorg Chem. 2005 Mar 07;44(5):1344-53. doi: 10.1021/ic0489443. PMID: 15732974.
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Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit.

The Journal of organic chemistry

Sakurai H, Ritonga MT, Shibatani H, Hirao T.
PMID: 15787569
J Org Chem. 2005 Apr 01;70(7):2754-62. doi: 10.1021/jo048324j.

[reaction: see text] Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles...

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Sakurai H, Ritonga MT, Shibatani H, et al. Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit. J Org Chem. 2005;70(7):2754-62doi: 10.1021/jo048324j.
Sakurai, H., Ritonga, M. T., Shibatani, H., & Hirao, T. (2005). Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit. The Journal of organic chemistry, 70(7), 2754-62. https://doi.org/10.1021/jo048324j
Sakurai, Hidehiro, et al. "Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit." The Journal of organic chemistry vol. 70,7 (2005): 2754-62. doi: https://doi.org/10.1021/jo048324j
Sakurai H, Ritonga MT, Shibatani H, Hirao T. Synthesis and characterization of p-phenylenediamine derivatives bearing an electron-acceptor unit. J Org Chem. 2005 Apr 01;70(7):2754-62. doi: 10.1021/jo048324j. PMID: 15787569.
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Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes.

Chemical communications (Cambridge, England)

Raw SA, Wilfred CD, Taylor RJ.
PMID: 14518877
Chem Commun (Camb). 2003 Sep 21;(18):2286-7. doi: 10.1039/b307177b.

Alpha-hydroxyketones undergo MnO2-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 1,2-dicarbonyl intermediates. Modifications of the...

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Raw SA, Wilfred CD, Taylor RJ. Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes. Chem Commun (Camb). 2003;(18):2286-7doi: 10.1039/b307177b.
Raw, S. A., Wilfred, C. D., & Taylor, R. J. (2003). Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes. Chemical communications (Cambridge, England), (18), 2286-7. https://doi.org/10.1039/b307177b
Raw, Steven A, et al. "Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes." Chemical communications (Cambridge, England) vol. ,18 (2003): 2286-7. doi: https://doi.org/10.1039/b307177b
Raw SA, Wilfred CD, Taylor RJ. Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes. Chem Commun (Camb). 2003 Sep 21;(18):2286-7. doi: 10.1039/b307177b. PMID: 14518877.
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Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives.

The Journal of organic chemistry

Xie C, Zhang Z, Li D, Gong J, Han X, Liu X, Ma C.
PMID: 28256123
J Org Chem. 2017 Apr 07;82(7):3491-3499. doi: 10.1021/acs.joc.6b02977. Epub 2017 Mar 13.

An efficient, green, and novel method for the synthesis of N-heterocycle-fused quinoxalines is reported herein. Dimethyl sulfoxide was used as both a reactant and a solvent in this reaction. A wide range of products in moderate to excellent yields...

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Xie C, Zhang Z, Li D, et al. Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives. J Org Chem. 2017;82(7):3491-3499doi: 10.1021/acs.joc.6b02977.
Xie, C., Zhang, Z., Li, D., Gong, J., Han, X., Liu, X., & Ma, C. (2017). Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives. The Journal of organic chemistry, 82(7), 3491-3499. https://doi.org/10.1021/acs.joc.6b02977
Xie, Caixia, et al. "Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives." The Journal of organic chemistry vol. 82,7 (2017): 3491-3499. doi: https://doi.org/10.1021/acs.joc.6b02977
Xie C, Zhang Z, Li D, Gong J, Han X, Liu X, Ma C. Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives. J Org Chem. 2017 Apr 07;82(7):3491-3499. doi: 10.1021/acs.joc.6b02977. Epub 2017 Mar 13. PMID: 28256123.
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Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: synthesis of benzannulated N-heterocycles by a cascade reaction.

Chemistry (Weinheim an der Bergstrasse, Germany)

Weiße M, Zille M, Jacob K, Schmidt R, Stolle A.
PMID: 25766865
Chemistry. 2015 Apr 20;21(17):6511-22. doi: 10.1002/chem.201406306. Epub 2015 Mar 12.

It was demonstrated that ortho-substituted anilines are prone to undergo hydroamination reactions with diethyl acetylenedicarboxylate in a planetary ball mill. A sequential coupling of the intermolecular hydroamination reaction with intramolecular ring closure was utilized for the syntheses of benzooxazines,...

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Weiße M, Zille M, Jacob K, et al. Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: synthesis of benzannulated N-heterocycles by a cascade reaction. Chemistry. 2015;21(17):6511-22doi: 10.1002/chem.201406306.
Weiße, M., Zille, M., Jacob, K., Schmidt, R., & Stolle, A. (2015). Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: synthesis of benzannulated N-heterocycles by a cascade reaction. Chemistry (Weinheim an der Bergstrasse, Germany), 21(17), 6511-22. https://doi.org/10.1002/chem.201406306
Weiße, Maik, et al. "Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: synthesis of benzannulated N-heterocycles by a cascade reaction." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,17 (2015): 6511-22. doi: https://doi.org/10.1002/chem.201406306
Weiße M, Zille M, Jacob K, Schmidt R, Stolle A. Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: synthesis of benzannulated N-heterocycles by a cascade reaction. Chemistry. 2015 Apr 20;21(17):6511-22. doi: 10.1002/chem.201406306. Epub 2015 Mar 12. PMID: 25766865.
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Showing 25 to 36 of 136 entries