1077-74-3Relevant articles and documents
Design and synthesis of 3-[(7-chloro-1-oxidoquinolin-4-ylamino)alkyl]-1,3- thiazolidin-4-ones as antimalarial agents
Solomon, V. Raja,Haq,Srivastava, Kumkum,Puri, Sunil K.,Katti
, p. 1048 - 1053 (2013)
A new series of quinoline analogs have been synthesized and found active against P. falciparum in vitro and P. yoelli in vivo. Compounds 8, 10 and 11 exhibited superior in vitro activity compared to chloroquine. Selected compounds 8, 10 and 11 exhibited significant suppression of parasitaemia in vivo assay. These analogs form a complex with hematin and inhibit the β-hematin formation, suggesting that this class of compounds act on a heme polymerization target. Further this study confirms that quinoline ring nitrogen is essential for both transportation of the molecule across the membrane as well as for tight binding to hematin.
Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal
, p. 5049 - 5055 (2021)
Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.
Regioselective Metal-Free Cross-Coupling of Quinoline N -Oxides with Boronic Acids
Bering, Luis,Antonchick, Andrey P.
, p. 3134 - 3137 (2015)
A novel and operationally simple one-step C-H bond functionalization of quinoline N-oxides to 2-substituted quinolines was developed. This approach enables the regioselective functionalization under external oxidant- and metal-free conditions. The developed transformation represents the first application of the Petasis reaction in functionalization of heterocycles.
Visible-Light-Promoted C2 Trifluoromethylation of Quinoline N -Oxides
Gao, Guo-Lin,Liang, Ce,Niu, Yan-Ning,Zhuo, Wang-Tao
, p. 219 - 226 (2020)
A photoredox catalytic strategy has been described for the direct C2 trifluoromethylation of quinoline N -oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2 tri
Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C-H activation
Ferlin, Francesco,Zangarelli, Agnese,Lilli, Simone,Santoro, Stefano,Vaccaro, Luigi
supporting information, p. 490 - 495 (2021/01/28)
Herein we present an efficient and regioselective iron-catalyzed methodology for the external oxidant-free functionalization of quinoline-N-oxides. The protocol, based on the use of inexpensive and easily accessible FeSO4, showed broad applicability to a wide range of substrates. An additional green feature of this synthetic methodology is H2O being the only by-product. Experimental and computational investigations provide support to a mechanism based on a facile C-H activation event. The green efficiency of the process has also been carefully assessed using: (i) metrics related to the synthetic process (AE, Yield, 1/SF, MRP and RME); (ii) safety/hazard metrics (SHZI and SHI); and (iii) metrics related to the metal used as the catalyst (Abundance, OEL and ADP). In addition to the many advantages of this protocol related to the green iron catalyst used and the safety/hazard features of the process, an E-factor value of ca. 0.92 (84 to >99% reduction compared to known protocols) evidently confirms the sustainable efficiency of the procedure presented. Practical utility has also been demonstrated by performing the reaction efficiently on a multi-gram scale. This journal is
Deoxygenative C2-heteroarylation of quinoline N-oxides: Facile access to α-Triazolylquinolines
Sontakke, Geetanjali S.,Shukla, Rahul K.,Volla, Chandra M. R.
supporting information, p. 485 - 493 (2021/03/22)
A metal-and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-Triazoles. A variety of α-Triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.
BIAMINOQUINOLINES AND NANOFORMULATIONS FOR CANCER TREATMENT
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Paragraph 0169, (2021/04/01)
The present invention provides bisaminoquinoline compounds of Formula (I). The present invention also provides nanocarriers comprising compounds of the present invention, and methods of using the nanocarriers for treating diseases and imaging.
Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions
Dhiman, Ankit Kumar,Thakur, Ankita,Kumar, Inder,Kumar, Rakesh,Sharma, Upendra
, p. 9244 - 9254 (2020/08/14)
A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.
A heterogeneous and recoverable palladium catalyst to access the regioselective C-H alkenylation of quinoline: N -oxides
Chen, Shaomin,Ferlin, Francesco,Gu, Yanlong,Piermatti, Oriana,Sciosci, Daniele,Vaccaro, Luigi,Valentini, Federica
supporting information, p. 6560 - 6566 (2020/11/09)
Herein, we disclose the first C-2-selective C-H alkenylation of quinoline N-oxides catalyzed using a heterogeneous palladium catalyst. The protocol does not require the use of an external oxidant and it is applicable to an ample substrate scope always showing excellent site selectivity. This process is made accessible by the use of a specific 1,2,3-triazolium-tagged heterogeneous polymeric catalytic system. The catalyst can be efficiently recovered and reused with no decrease of its catalytic performance and hot filtration and mercury poisoning tests suggest that its mechanism of action is operatively heterogeneous. In addition, mechanistic studies revealed that C-H activation reaction pathways are operative, setting the stage for the direct synthesis of 2-functionalized quinolines using N-oxide functionality as both a directing group and an oxidant.
Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions
Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh
supporting information, p. 5616 - 5625 (2019/11/22)
A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).
