93501-08-7Relevant academic research and scientific papers
Cobalt-catalyzed carbonylative cyclization of N-(2-Vinylphenyl)nicotinamides to access (NH)-quinolin-2(1H)-ones
Wu, Xiao-Feng,Ying, Jun,Zhu, Yiwen
, (2022/04/12)
A cobalt-catalyzed carbonylative cyclization of N-(2-vinylphenyl)picolinamides for the construction of (NH)-quinolin-2(1H)-one scaffolds has been developed. In this reaction, various free (NH)-quinolin-2(1H)-ones were produced in good yields (up to 92%) by employing benzene-1,3,5-triyl triformate (TFBen) as the CO source and picolinamide as the traceless directing group. Moreover, several synthetic transformations of the obtained (NH)-quinolin-2(1H)-ones were performed and a facile and rapid access to the core skeleton of Tipifarnib was realized to demonstrate the utility of this protocol.
1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides
Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna
, p. 2080 - 2084 (2021/10/07)
Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.
Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents
Nan, Jiang,Chen, Pu,Gong, Xue,Hu, Yan,Ma, Qiong,Wang, Bo,Ma, Yangmin
supporting information, p. 3761 - 3766 (2021/05/10)
A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.
Palladium-catalyzed arylation/cyclization/desulfonation cascades toward 4-aryl quinolin-2(1H)-ones with diaryliodonium salts
Han, Jianwei,Wu, Xunshen,Zhang, Zhiang,Wang, Limin
supporting information, p. 3433 - 3436 (2017/08/08)
Palladium-catalyzed cascades of arylation/cyclization/desulfonation of ortho-aminocinnamate esters by using diaryliodonium salts afforded a wide range of 4-aryl quinolin-2(1H)-ones. As such, the desired 4-aryl quinolin-2(1H)-ones with potential biological activity has been synthesized in the yields of 34–96%.
Method for preparing 4-aryl-2-quinolinone through carbon dioxide
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Paragraph 0045; 0046; 0047, (2017/04/03)
The invention discloses a method for preparing 4-aryl-2-quinolinone through carbon dioxide, and belongs to the technical field of carbon dioxide comprehensive utilization. The method comprises the following concrete process steps: in a dehydrated and deox
Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2towards 4-Aryl-2-Quinolinones
Sun, Song,Hu, Wei-Ming,Gu, Ning,Cheng, Jiang
supporting information, p. 18729 - 18732 (2016/12/26)
A palladium-catalyzed three-component reaction between N-tosylhydrazones, 2-iodoanilines and atmospheric pressure CO2was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4-aryl-2-quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C?C, one C=C and one C?N (amide), representing an efficient methodology for incorporation of CO2into heterocycles.
Synthesis of 4-Aryl-2-Quinolones via Copper-Catalyzed Hydroarylation of (o-Aminophenyl)propiolates with Arylboronates
Murayama, Tsukasa,Shibuya, Masatoshi,Yamamoto, Yoshihiko
, p. 166 - 171 (2016/02/14)
4-Aryl-2(1H)-quinolones were efficiently synthesized via copper-catalyzed hydroarylation of (o-aminophenyl)propiolates with arylboronic acid neopentyl glycol esters. The substrate propiolates were prepared from the corresponding silylalkynes with carbon d
Practical route to 2-quinolinones via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade reaction
Wu, Junliang,Xiang, Shaohua,Zeng, Jing,Leow, Minli,Liu, Xue-Wei
supporting information, p. 222 - 225 (2015/01/30)
Quinolinone derivatives were constructed via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.
A straight forward synthesis of 4-aryl substituted 2-quinolones via Heck reaction
Gupta, Sumanta,Ganguly, Bhaskar,Das, Sajal
, p. 41148 - 41151 (2015/02/05)
A variety of aryl halides have been successfully coupled with different olefins via Heck reaction in the presence of an active stimulant (Pd-NHC). An efficient one pot protocol for the easy access of structurally diverse 4-aryl-2-quinolones via domino Heck/cyclization reaction has been developed. This journal is
4-Aryl-2-quinolones via a domino heck reaction/cyclization process
Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Sferrazza, Alessio
, p. 99 - 105 (2008/02/08)
The reaction of methyl β-(o-acetamidophenyl)acrylates with aryl iodides in the presence of Pd(OAc)2 and KOAc in DMF at 120 °C affords 4-aryl-2-quinolones in allowable to good yields.
