- 4(1H)-quinolinone alkaloids an efficient synthesis of graveoline by palladium-catalysed reductive N-heterocyclisation
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An efficient synthesis of the 4H-quinolone alkaloid graveoline has been achieved by a route featuring an Pd(II)-catalysed reductive N-heterocyclisatton [ CO(3 MPa), Pd(TMB)2, TMPhen, 170 °C, 3h] of 2′-nitrochalcone as a key step.
- Annunziata,Cenini,Palmisano,Tollari
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Read Online
- QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF
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The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]
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Paragraph 00049
(2022/03/21)
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- Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F
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An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.
- Mehta, Goverdhan,Nerella, Sharanya,Pabbaraja, Srihari,Singh, Shweta
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supporting information
(2020/02/22)
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- Novel synthesis of graveoline and graveolinine
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Cyclization of 2-aryl amides with base lead to quinolone derivatives. Both graveoline and graveolinine were synthesized.GRAPHICAL ABSTRACT (Figure presented.).
- Bandatmakuru, Sreenivasula Reddy,Arava, Veera Reddy
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p. 2635 - 2641
(2018/10/31)
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- Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones
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A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl2, a C(3) zincation is observed, whereas in the presence of MgCl2 or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.
- Klier, Lydia,Bresser, Tomke,Nigst, Tobias A.,Karaghiosoff, Konstantin,Knochel, Paul
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supporting information; experimental part
p. 13584 - 13587
(2012/10/08)
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- Short step synthesis of natural 2-arylquinolones based on iridium-catalyzed three-component coupling quinoline synthesis
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Eduline (la), graveoline (1b), and 6-methoxy-2-(4-methoxyphenyl)-1-methylquinolone (1c) were synthesized by iridium-catalyzed three-component coupling reaction. Reaction of an aniline, an aromatic aldehyde, and acetaldehyde gave the corresponding substitu
- Nakajima, Takayuki,Inada, Takashi,Shimizu, Isao
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p. 497 - 504
(2008/02/03)
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- Synthesis of 2-arylquinoline and 2-aryl-4-quinolone alkaloids via Diels- Alder reaction of 1,2,3-benzotriazine with enamines
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Synthesis of the 2-arylquinoline alkaloids, 2-phenylquinoline and dubamine, and the 2-arylquinolone alkaloids, 1-methyl-2-phenyl-4-quinolone, graveoline, reevesianine-A, and eduline, was accomplished by the Diels-Alder reaction of 1,2,3-benzotriazine with enamines as a key step.
- Koyama, Junko,Toyokuni, Izumi,Tagahara, Kiyoshi
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p. 1038 - 1039
(2007/10/03)
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- A SIMPLE REGIOSELECTIVE PREPARATION OF 2- OR 3-SUBSTITUTED QUINOLINE DERIVATIVES VIA DIALKYLQUINOLYLBORANES
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Various quinoline derivatives possessing a substituent at the 2- or 3-position were prepared by the reaction of dialkylquinolylboranes and organic bromides in the presence of a palladium catalyst.
- Ishikura, Minoru,Oda, Izumi,Terashima, Masanao
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p. 2375 - 2386
(2007/10/02)
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- The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 9. Synthesis of 2-Arylquinoline Alkaloids
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A one-step synthesis of N-methyl-2-aryl-4-quinolone alkaloids is described.These compounds are readily prepared from the reaction of an N-methylisatoic anhydride with the lithium enolate of an acetophenone.By this method, the reaction of N-methylisatoic a
- Coppola, Gary M.
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p. 727 - 731
(2007/10/02)
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