485-61-0Relevant academic research and scientific papers
4(1H)-quinolinone alkaloids an efficient synthesis of graveoline by palladium-catalysed reductive N-heterocyclisation
Annunziata,Cenini,Palmisano,Tollari
, p. 495 - 501 (1996)
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.
QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF
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Paragraph 00049, (2022/03/21)
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]
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
Mehta, Goverdhan,Nerella, Sharanya,Pabbaraja, Srihari,Singh, Shweta
supporting information, (2020/02/22)
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.
Novel synthesis of graveoline and graveolinine
Bandatmakuru, Sreenivasula Reddy,Arava, Veera Reddy
, p. 2635 - 2641 (2018/10/31)
Cyclization of 2-aryl amides with base lead to quinolone derivatives. Both graveoline and graveolinine were synthesized.GRAPHICAL ABSTRACT (Figure presented.).
Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones
Klier, Lydia,Bresser, Tomke,Nigst, Tobias A.,Karaghiosoff, Konstantin,Knochel, Paul
supporting information; experimental part, p. 13584 - 13587 (2012/10/08)
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.
Short step synthesis of natural 2-arylquinolones based on iridium-catalyzed three-component coupling quinoline synthesis
Nakajima, Takayuki,Inada, Takashi,Shimizu, Isao
, p. 497 - 504 (2008/02/03)
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
Synthesis of 2-arylquinoline and 2-aryl-4-quinolone alkaloids via Diels- Alder reaction of 1,2,3-benzotriazine with enamines
Koyama, Junko,Toyokuni, Izumi,Tagahara, Kiyoshi
, p. 1038 - 1039 (2007/10/03)
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.
A SIMPLE REGIOSELECTIVE PREPARATION OF 2- OR 3-SUBSTITUTED QUINOLINE DERIVATIVES VIA DIALKYLQUINOLYLBORANES
Ishikura, Minoru,Oda, Izumi,Terashima, Masanao
, p. 2375 - 2386 (2007/10/02)
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.
The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 9. Synthesis of 2-Arylquinoline Alkaloids
Coppola, Gary M.
, p. 727 - 731 (2007/10/02)
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
