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Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization.

Chemical record (New York, N.Y.)

Chelucci G, Porcheddu A.
PMID: 27524555
Chem Rec. 2017 Feb;17(2):200-216. doi: 10.1002/tcr.201600083. Epub 2016 Aug 15.

Efficient ruthenium-, rhodium-, palladium-, copper- and iridium-catalysed methodologies have been recently developed for the synthesis of quinolines by the reaction of 2-aminobenzyl alcohols with carbonyl compounds (aldehydes and ketones) or the related alcohols. The reaction is assumed to proceed...

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Chelucci G, Porcheddu A. Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chem Rec. 2016;17(2):200-216doi: 10.1002/tcr.201600083.
Chelucci, G., & Porcheddu, A. (2017). Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chemical record (New York, N.Y.), 17(2), 200-216. https://doi.org/10.1002/tcr.201600083
Chelucci, Giorgio, and Porcheddu, Andrea. "Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization." Chemical record (New York, N.Y.) vol. 17,2 (2017): 200-216. doi: https://doi.org/10.1002/tcr.201600083
Chelucci G, Porcheddu A. Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chem Rec. 2017 Feb;17(2):200-216. doi: 10.1002/tcr.201600083. Epub 2016 Aug 15. PMID: 27524555.
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Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines.

Organic letters

Kumar GS, Kumar P, Kapur M.
PMID: 28448156
Org Lett. 2017 May 19;19(10):2494-2497. doi: 10.1021/acs.orglett.7b00715. Epub 2017 Apr 27.

A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino...

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Kumar GS, Kumar P, Kapur M. Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines. Org Lett. 2017;19(10):2494-2497doi: 10.1021/acs.orglett.7b00715.
Kumar, G. S., Kumar, P., & Kapur, M. (2017). Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines. Organic letters, 19(10), 2494-2497. https://doi.org/10.1021/acs.orglett.7b00715
Kumar, Gangam Srikanth, et al. "Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines." Organic letters vol. 19,10 (2017): 2494-2497. doi: https://doi.org/10.1021/acs.orglett.7b00715
Kumar GS, Kumar P, Kapur M. Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines. Org Lett. 2017 May 19;19(10):2494-2497. doi: 10.1021/acs.orglett.7b00715. Epub 2017 Apr 27. PMID: 28448156.
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Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines.

Chemical communications (Cambridge, England)

Kuwano R, Ikeda R, Hirasada K.
PMID: 25847758
Chem Commun (Camb). 2015 May 01;51(35):7558-61. doi: 10.1039/c5cc01971k.

The reduction of quinolines selectively took place on their carbocyclic rings to give 5,6,7,8-tetrahydroquinolines, when the hydrogenation was conducted in the presence of a Ru(η(3)-methallyl)2(cod)-PhTRAP catalyst. The chiral ruthenium catalyst converted 8-substituted quinolines into chiral 5,6,7,8-tetrahydroquinolines with up to...

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Kuwano R, Ikeda R, Hirasada K. Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines. Chem Commun (Camb). 2015;51(35):7558-61doi: 10.1039/c5cc01971k.
Kuwano, R., Ikeda, R., & Hirasada, K. (2015). Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines. Chemical communications (Cambridge, England), 51(35), 7558-61. https://doi.org/10.1039/c5cc01971k
Kuwano, Ryoichi, et al. "Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines." Chemical communications (Cambridge, England) vol. 51,35 (2015): 7558-61. doi: https://doi.org/10.1039/c5cc01971k
Kuwano R, Ikeda R, Hirasada K. Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines. Chem Commun (Camb). 2015 May 01;51(35):7558-61. doi: 10.1039/c5cc01971k. PMID: 25847758.
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Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.

The Journal of organic chemistry

Evoniuk CJ, Gomes GDP, Ly M, White FD, Alabugin IV.
PMID: 28357857
J Org Chem. 2017 Apr 21;82(8):4265-4278. doi: 10.1021/acs.joc.7b00262. Epub 2017 Apr 03.

Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics. This...

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Evoniuk CJ, Gomes GDP, Ly M, et al. Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals. J Org Chem. 2017;82(8):4265-4278doi: 10.1021/acs.joc.7b00262.
Evoniuk, C. J., Gomes, G. D. P., Ly, M., White, F. D., & Alabugin, I. V. (2017). Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals. The Journal of organic chemistry, 82(8), 4265-4278. https://doi.org/10.1021/acs.joc.7b00262
Evoniuk, Christopher J, et al. "Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals." The Journal of organic chemistry vol. 82,8 (2017): 4265-4278. doi: https://doi.org/10.1021/acs.joc.7b00262
Evoniuk CJ, Gomes GDP, Ly M, White FD, Alabugin IV. Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals. J Org Chem. 2017 Apr 21;82(8):4265-4278. doi: 10.1021/acs.joc.7b00262. Epub 2017 Apr 03. PMID: 28357857.
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Calcium Hydride Catalyzed Highly 1,2-Selective Pyridine Hydrosilylation.

Chemistry (Weinheim an der Bergstrasse, Germany)

Intemann J, Bauer H, Pahl J, Maron L, Harder S.
PMID: 26120024
Chemistry. 2015 Aug 03;21(32):11452-61. doi: 10.1002/chem.201501072. Epub 2015 Jun 26.

Reaction of the calcium hydride complex (DIPPnacnac-CaH⋅THF)2 with pyridine is much faster and selective than that of the corresponding magnesium hydride complex (DIPPnacnac = [(2,6-iPr2 C6 H3 )NC(Me)]2 CH). With a range of pyridine, picoline and quinoline substrates, exclusive...

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Intemann J, Bauer H, Pahl J, et al. Calcium Hydride Catalyzed Highly 1,2-Selective Pyridine Hydrosilylation. Chemistry. 2015;21(32):11452-61doi: 10.1002/chem.201501072.
Intemann, J., Bauer, H., Pahl, J., Maron, L., & Harder, S. (2015). Calcium Hydride Catalyzed Highly 1,2-Selective Pyridine Hydrosilylation. Chemistry (Weinheim an der Bergstrasse, Germany), 21(32), 11452-61. https://doi.org/10.1002/chem.201501072
Intemann, Julia, et al. "Calcium Hydride Catalyzed Highly 1,2-Selective Pyridine Hydrosilylation." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,32 (2015): 11452-61. doi: https://doi.org/10.1002/chem.201501072
Intemann J, Bauer H, Pahl J, Maron L, Harder S. Calcium Hydride Catalyzed Highly 1,2-Selective Pyridine Hydrosilylation. Chemistry. 2015 Aug 03;21(32):11452-61. doi: 10.1002/chem.201501072. Epub 2015 Jun 26. PMID: 26120024.
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Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles.

Journal of the American Chemical Society

Cui X, Li Y, Bachmann S, Scalone M, Surkus AE, Junge K, Topf C, Beller M.
PMID: 26230874
J Am Chem Soc. 2015 Aug 26;137(33):10652-8. doi: 10.1021/jacs.5b05674. Epub 2015 Aug 11.

An important goal for nanocatalysis is the development of flexible and efficient methods for preparing active and stable core-shell catalysts. In this respect, we present the synthesis and characterization of iron oxides surrounded by nitrogen-doped-graphene shells immobilized on carbon...

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Cui X, Li Y, Bachmann S, et al. Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles. J Am Chem Soc. 2015;137(33):10652-8doi: 10.1021/jacs.5b05674.
Cui, X., Li, Y., Bachmann, S., Scalone, M., Surkus, A. E., Junge, K., Topf, C., & Beller, M. (2015). Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles. Journal of the American Chemical Society, 137(33), 10652-8. https://doi.org/10.1021/jacs.5b05674
Cui, Xinjiang, et al. "Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles." Journal of the American Chemical Society vol. 137,33 (2015): 10652-8. doi: https://doi.org/10.1021/jacs.5b05674
Cui X, Li Y, Bachmann S, Scalone M, Surkus AE, Junge K, Topf C, Beller M. Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles. J Am Chem Soc. 2015 Aug 26;137(33):10652-8. doi: 10.1021/jacs.5b05674. Epub 2015 Aug 11. PMID: 26230874.
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Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes.

Chemical communications (Cambridge, England)

Das A, Ghosh I, König B.
PMID: 27333456
Chem Commun (Camb). 2016 Jul 05;52(56):8695-8. doi: 10.1039/c6cc04366f.

1-(2-Bromophenyl)-1H-pyrrole and 1-(2,6-dibromophenyl)-1H-pyrrole react in the presence of catalytic amounts of rhodamine 6G () and N,N-diisopropylethylamine (DIPEA) under blue light irradiation with aromatic alkynes and subsequently cyclize intramolecularly to form pyrrolo[1,2-a]quinoline and ullazines. The reactions proceed at room temperature,...

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Das A, Ghosh I, König B. Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes. Chem Commun (Camb). 2016;52(56):8695-8doi: 10.1039/c6cc04366f.
Das, A., Ghosh, I., & König, B. (2016). Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes. Chemical communications (Cambridge, England), 52(56), 8695-8. https://doi.org/10.1039/c6cc04366f
Das, Amrita, et al. "Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes." Chemical communications (Cambridge, England) vol. 52,56 (2016): 8695-8. doi: https://doi.org/10.1039/c6cc04366f
Das A, Ghosh I, König B. Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes. Chem Commun (Camb). 2016 Jul 05;52(56):8695-8. doi: 10.1039/c6cc04366f. PMID: 27333456.
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Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines.

Organic letters

Tan Z, Jiang H, Zhang M.
PMID: 27300088
Org Lett. 2016 Jul 01;18(13):3174-7. doi: 10.1021/acs.orglett.6b01390. Epub 2016 Jun 14.

A new benzylation protocol, enabling straightforward access to β-benzylated quinolines, has been demonstrated. By employing readily available [RuCl2(p-cymene)]2 as a catalyst and O2 as a sole green oxidant, various 1,2,3,4-tetrahydroquinolines were efficiently converted in combination with aryl aldehydes into...

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Tan Z, Jiang H, Zhang M. Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines. Org Lett. 2016;18(13):3174-7doi: 10.1021/acs.orglett.6b01390.
Tan, Z., Jiang, H., & Zhang, M. (2016). Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines. Organic letters, 18(13), 3174-7. https://doi.org/10.1021/acs.orglett.6b01390
Tan, Zhenda, et al. "Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines." Organic letters vol. 18,13 (2016): 3174-7. doi: https://doi.org/10.1021/acs.orglett.6b01390
Tan Z, Jiang H, Zhang M. Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines. Org Lett. 2016 Jul 01;18(13):3174-7. doi: 10.1021/acs.orglett.6b01390. Epub 2016 Jun 14. PMID: 27300088.
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Evaluation of the electronic properties of perfluorophenyl functionalized quinolines and their hybrids with carbon nanostructures.

Physical chemistry chemical physics : PCCP

Sygellou L, Kakogianni S, Andreopoulou AK, Theodosiou K, Leftheriotis G, Kallitsis JK, Siokou A.
PMID: 26781962
Phys Chem Chem Phys. 2016 Feb 07;18(5):4154-65. doi: 10.1039/c5cp06016h.

Hybrid materials based on perfluorophenyl functionalized quinolines directly attached onto the sp(2) hybridized surface of carbon nanostructures have been prepared and studied herein along with their precursor semiconducting small molecules. Tails of different polarities have been used so that...

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Sygellou L, Kakogianni S, Andreopoulou AK, et al. Evaluation of the electronic properties of perfluorophenyl functionalized quinolines and their hybrids with carbon nanostructures. Phys Chem Chem Phys. 2016;18(5):4154-65doi: 10.1039/c5cp06016h.
Sygellou, L., Kakogianni, S., Andreopoulou, A. K., Theodosiou, K., Leftheriotis, G., Kallitsis, J. K., & Siokou, A. (2016). Evaluation of the electronic properties of perfluorophenyl functionalized quinolines and their hybrids with carbon nanostructures. Physical chemistry chemical physics : PCCP, 18(5), 4154-65. https://doi.org/10.1039/c5cp06016h
Sygellou, Lambrini, et al. "Evaluation of the electronic properties of perfluorophenyl functionalized quinolines and their hybrids with carbon nanostructures." Physical chemistry chemical physics : PCCP vol. 18,5 (2016): 4154-65. doi: https://doi.org/10.1039/c5cp06016h
Sygellou L, Kakogianni S, Andreopoulou AK, Theodosiou K, Leftheriotis G, Kallitsis JK, Siokou A. Evaluation of the electronic properties of perfluorophenyl functionalized quinolines and their hybrids with carbon nanostructures. Phys Chem Chem Phys. 2016 Feb 07;18(5):4154-65. doi: 10.1039/c5cp06016h. PMID: 26781962.
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Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines.

Journal of the American Chemical Society

Ji P, Feng X, Veroneau SS, Song Y, Lin W.
PMID: 29041776
J Am Chem Soc. 2017 Nov 08;139(44):15600-15603. doi: 10.1021/jacs.7b09093. Epub 2017 Oct 25.

We report the quantitative conversion of [M

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Ji P, Feng X, Veroneau SS, et al. Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines. J Am Chem Soc. 2017;139(44):15600-15603doi: 10.1021/jacs.7b09093.
Ji, P., Feng, X., Veroneau, S. S., Song, Y., & Lin, W. (2017). Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines. Journal of the American Chemical Society, 139(44), 15600-15603. https://doi.org/10.1021/jacs.7b09093
Ji, Pengfei, et al. "Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines." Journal of the American Chemical Society vol. 139,44 (2017): 15600-15603. doi: https://doi.org/10.1021/jacs.7b09093
Ji P, Feng X, Veroneau SS, Song Y, Lin W. Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines. J Am Chem Soc. 2017 Nov 08;139(44):15600-15603. doi: 10.1021/jacs.7b09093. Epub 2017 Oct 25. PMID: 29041776.
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Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis.

The Journal of organic chemistry

Aylward N, Kvaskoff D, Becker J, Wentrup C.
PMID: 27152548
J Org Chem. 2016 Jun 03;81(11):4609-15. doi: 10.1021/acs.joc.6b00444. Epub 2016 May 13.

The relationship between 4-quinolylcarbene 17, 3-quinolylcarbene 21, 2-quinolylcarbene 25, and 1-naphthylnitrene 35 has been explored experimentally and computationally. The diazomethylquinolines generated from (5-tetrazolyl)quinolines or 1,2,3-triazolo[1,5-a]quinoline by conventional flash vacuum pyrolysis (FVP) were observed by IR spectroscopy. The carbenes were...

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Aylward N, Kvaskoff D, Becker J, et al. Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis. J Org Chem. 2016;81(11):4609-15doi: 10.1021/acs.joc.6b00444.
Aylward, N., Kvaskoff, D., Becker, J., & Wentrup, C. (2016). Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis. The Journal of organic chemistry, 81(11), 4609-15. https://doi.org/10.1021/acs.joc.6b00444
Aylward, Nigel, et al. "Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis." The Journal of organic chemistry vol. 81,11 (2016): 4609-15. doi: https://doi.org/10.1021/acs.joc.6b00444
Aylward N, Kvaskoff D, Becker J, Wentrup C. Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis. J Org Chem. 2016 Jun 03;81(11):4609-15. doi: 10.1021/acs.joc.6b00444. Epub 2016 May 13. PMID: 27152548.
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Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines.

Organic letters

Saunthwal RK, Patel M, Verma AK.
PMID: 27119774
Org Lett. 2016 May 06;18(9):2200-3. doi: 10.1021/acs.orglett.6b00817. Epub 2016 Apr 27.

A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups...

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Saunthwal RK, Patel M, Verma AK. Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines. Org Lett. 2016;18(9):2200-3doi: 10.1021/acs.orglett.6b00817.
Saunthwal, R. K., Patel, M., & Verma, A. K. (2016). Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines. Organic letters, 18(9), 2200-3. https://doi.org/10.1021/acs.orglett.6b00817
Saunthwal, Rakesh K, et al. "Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines." Organic letters vol. 18,9 (2016): 2200-3. doi: https://doi.org/10.1021/acs.orglett.6b00817
Saunthwal RK, Patel M, Verma AK. Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines. Org Lett. 2016 May 06;18(9):2200-3. doi: 10.1021/acs.orglett.6b00817. Epub 2016 Apr 27. PMID: 27119774.
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