4179-37-7Relevant academic research and scientific papers
QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF
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Paragraph 00050, (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]
NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
, p. 7772 - 7779 (2021/06/30)
Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
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
, (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.
Synthesis, in vitro and in vivo biological evaluation of novel graveolinine derivatives as potential anti-Alzheimer agents
Luo, Wen,Lv, Jian-Wu,Wang, Ting,Zhang, Zhi-Yang,Guo, Hui-Yan,Song, Zhi-Yi,Wang, Chao-Jie,Ma, Jing,Chen, Yi-ping
, (2019/11/29)
A novel series of graveolinine derivatives were synthesized and evaluated as potential anti-Alzheimer agents. Compound 5f exhibited the best inhibitory activity for acetylcholinesterase (AChE) and had surprisingly potent inhibitory activity for butyrylcho
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.).
Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji–Trost Reaction
Wang, Kang,Ping, Yifan,Chang, Taiwei,Wang, Jianbo
supporting information, p. 13140 - 13144 (2017/10/11)
Vinyl chromium(0) Fischer carbene complexes were employed as the source of π-allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six-membered heterocyclic flavonones and quinolines are obtained, depending on the nucleophilic functional group on the coupling partners.
Lewis Acid Promoted Oxonium Ion Driven Carboamination of Alkynes for the Synthesis of 4-Alkoxy Quinolines
Gharpure, Santosh J.,Nanda, Santosh K.,Adate, Priyanka A.,Shelke, Yogesh G.
, p. 2067 - 2080 (2017/02/26)
Lewis acid mediated multisegment coupling cascade is designed for the synthesis of densely substituted 4-alkoxy quinolines via an oxonium ion triggered alkyne carboamination sequence involving C-C and C-N bond formations. Cyclic ether fused-quinolines cou
Revealing the Macromolecular Targets of Fragment-Like Natural Products
Rodrigues, Tiago,Reker, Daniel,Kunze, Jens,Schneider, Petra,Schneider, Gisbert
, p. 10516 - 10520 (2015/09/02)
Fragment-like natural products were identified as ligand-efficient chemical matter for hit-to-lead development and chemical-probe discovery. Relying on a computational method using a topological pharmacophore descriptor and a drug database, several macromolecular targets from distinct protein families were expeditiously retrieved for structurally unrelated chemotypes. The selected fragments feature structural dissimilarity to the reference compounds and suitable target affinity, and they offer opportunities for chemical optimization. Experimental confirmation of hitherto unknown macromolecular targets for the selected molecules corroborate the usefulness of the computational approach and suggests broad applicability to chemical biology and molecular medicine. Target acquired: Hitherto unknown macromolecular targets of the fragment-like natural products goitrin, isomacroin, and graveolinine were discovered through the use of a computational target-prediction tool tailored for natural products. The results suggest that such methods will find application in target discovery for natural products and could inspire the design of new chemical entities for chemical biology and molecular medicine.
Hypervalent iodine oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones: An expedient route to naturally occurring 4-alkoxy-2-arylquinolines
Varma, Rajender S.,Kumar, Dalip
, p. 9113 - 9116 (2007/10/03)
Easily accessible 2-aryl-1,2,3,4-tetrahydro-4-quinolones are readily oxidized to the corresponding 4-alkoxy-2-arylquinolines using a relatively safe hypervalent iodine reagent, [hydroxy (tosyloxy)iodo]benzene (HTIB), in high yields, thus providing a conci
APPLICATION OF THE LEWIS ACID CATALYZED CYCLOADDITION REACTION TO SYNTHESIS OF NATURAL QUINOLINE ALKALOIDS
Kametani, Tetsuji,Takeda, Hajime,Suzuki, Yukio,Kasai, Hiroko (nee Furuyama),Honda, Toshio
, p. 3385 - 3395 (2007/10/02)
Lewis acids catalyzed cycloaddition reaction of the Schiff base with the olefin was applied to the syntheses of some natural quinoline alkaloids.The extension of cycloaddition using the acetal and the orthoester as dienophiles or using s-triazin
