- Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes
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The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.
- Lou, Shao-Jie,Luo, Gen,Yamaguchi, Shigeru,An, Kun,Nishiura, Masayoshi,Hou, Zhaomin
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supporting information
p. 20462 - 20471
(2021/12/03)
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- Visible-Light-Induced Amination of Quinoline at the C8 Position via a Postcoordinated Interligand-Coupling Strategy under Mild Conditions
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The postcoordinated interligand-coupling strategy provides a useful and complementary protocol for synthesizing polydentate ligands. Herein, diastereoselective photoreactions of Λ-[Ir(pq)2(d-AA)] (Λ-d) and Λ-[Ir(pq)2(l-AA)] (Λ-l, where pq is 2-phenylquino
- Peng, He-Long,Li, Yinwu,Chen, Xing-Yang,Li, Li-Ping,Ke, Zhuofeng,Ye, Bao-Hui
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p. 908 - 918
(2021/02/05)
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- Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide
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Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.
- Naruto, Hiroki,Togo, Hideo
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p. 1122 - 1130
(2020/04/01)
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- Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
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A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of commercially available chemicals as starting materials, an inexpensive metal catalyst, aerobic reaction conditions, tolerance of a wide range of functional groups, and operational simplicity are the notable advantages of this present protocol.
- Mahato, Sachinta,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
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p. 7907 - 7917
(2019/09/06)
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- Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines
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A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.
- Xu, Jingxiu,Sun, Jing,Zhao, Jinwu,Huang, Bin,Li, Xiaohan,Sun, Yulun
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p. 36242 - 36245
(2017/08/02)
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- Synthesis of quinolines through copper-catalyzed intermolecular cyclization reaction from anilines and terminal acetylene esters
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A simple and convenient copper-catalyzed intermolecular cyclization reaction for the synthesis of quinolines from anilines and terminal acetylene esters has been developed. This methodology constructs the C-N and C-C bonds successively via a cascade process, and provides the desired products in moderate to good yields.
- Zheng, Zhilei,Deng, Guobo,Liang, Yun
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p. 103478 - 103481
(2016/11/13)
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- Synthesis of quinoline derivatives by an improved D?ebner-von Miller reaction using a recyclable Ag(I)-exchanged Montmorillonite K10 catalyst
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The D?ebner-von Miller synthesis of quinolines under solvent-free conditions is described, catalyzed by recyclable Ag(I)-exchanged Montmorillonite K10. The desired products are obtained in good to excellent yields and the reaction accommodates both aromatic and aliphatic α,β-unsaturated aldehydes making this process an attractive method for the synthesis of substituted quinolines. In addition, the Ag(I)-exchanged Montmorillonite K10 catalyst can be recovered and reused up to 5 times with excellent activity.
- Jayram, Janeeka,Jeena, Vineet
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p. 2213 - 2224
(2017/02/10)
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- An efficient synthesis of quinolines via copper-catalyzed C-N cleavage
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An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of su
- Xi, Long-Yi,Zhang, Ruo-Yi,Zhang, Lei,Chen, Shan-Yong,Yu, Xiao-Qi
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p. 3924 - 3930
(2015/03/30)
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- Synthesis of substituted quinoline via copper-catalyzed one-pot cascade reactions of 2-bromobenzaldehydes with aryl methyl ketones and aqueous ammonia
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In this Letter, a new version of the Friedl?nder synthesis of quinoline derivatives starting from 2-bromobenzaldehydes, aryl methyl ketones, and aqueous ammonia with copper-catalyzed amination as a key step is presented. Remarkable advantages of this new quinoline synthesis include commercially available and economical starting materials, simple operational process, and excellent efficiency.
- Li, Bin,Guo, Chenhao,Fan, Xuesen,Zhang, Ju,Zhang, Xinying
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supporting information
p. 5944 - 5948
(2015/01/08)
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- Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization-aromatization approach
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A microwave-assisted solid acid-catalyzed synthesis of quinolines from anilines and cinnamaldehydes is described. Use of montmorillonite K-10 results in a one-pot process; the cyclization and oxidation steps readily take place in a domino approach. Reactions were completed in a matter of minutes and provided excellent yields. The efficient and ecofriendly catalyst and the convenience of the product isolation make this process an attractive alternative for the synthesis of these important heterocycles.
- De Paolis, Omar,Teixeira, Liliana,T?r?k, Béla
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experimental part
p. 2939 - 2942
(2009/07/26)
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- Novel 2-phenylquinolin-7-yl-derived imidazo[1,5-a]pyrazines as potent insulin-like growth factor-I receptor (IGF-IR) inhibitors
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A series of novel, potent quinolinyl-derived imidazo[1,5-a]pyrazine IGF-IR (IGF-1R) inhibitors-most notably, cis-3-(3-azetidin-1-ylmethylcyclobutyl)-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-ylamine (AQIP)-is described. Synthetic details, structure
- Mulvihill, Mark J.,Ji, Qun-Sheng,Coate, Heather R.,Cooke, Andrew,Dong, Hanqing,Feng, Lixin,Foreman, Kenneth,Rosenfeld-Franklin, Maryland,Honda, Ayako,Mak, Gilda,Mulvihill, Kristen M.,Nigro, Anthony I.,O'Connor, Matthew,Pirrit, Caroline,Steinig, Arno G.,Siu, Kam,Stolz, Kathryn M.,Sun, Yingchuan,Tavares, Paula A.R.,Yao, Yan,Gibson, Neil W.
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p. 1359 - 1375
(2008/09/19)
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- A Novel Approach to 2-Arylated Quinolines: Electrocyclization of Alkynyl Imines via Vinylidene Complexes
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(Matrix presented) Alkynyl imines underwent [4 + 2] electrocyclization in the presence of 20 mol % W(CO)5(THF) to give 2-arylated quinolines in good yields. A deuterium labeling study suggests that the reaction proceeds via a tungsten vinylidene complex.
- Sangu, Kenichiro,Fuchibe, Kohei,Akiyama, Takahiko
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p. 353 - 355
(2007/10/03)
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- Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
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o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.
- Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
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p. 13397 - 13418
(2007/10/03)
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