106015-75-2Relevant academic research and scientific papers
4-Aryl-2-quinolones via a domino heck reaction/cyclization process
Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Sferrazza, Alessio
, p. 99 - 105 (2006)
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.
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
supporting information, 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.
Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives
Krishna Reddy, Singarajanahalli Mundarinti,Prasanna Kumari, Subramaniyan,Selva Ganesan, Subramaniapillai
, (2021/08/03)
Palladium catalysed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biologically significant 4-arylquinolin-2-one or pyrazolone derivatives. The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety in the acetonitrile also converted to the corresponding acetophenone derivative.
Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones
Basuli, Scuhand,Satyanarayana, Gedu
, p. 957 - 970 (2017/12/07)
Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple, bench-top aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation. Significantly, the strategy was extended to the domino one-pot synthesis of drugs and bioactive compounds.
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%.
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.
Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral
Zhang, Zhen,Liao, Li-Li,Yan, Si-Shun,Wang, Lei,He, Yun-Qi,Ye, Jian-Heng,Li, Jing,Zhi, Yong-Gang,Yu, Da-Gang
supporting information, p. 7068 - 7072 (2016/07/06)
The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.
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.
