60657-74-1Relevant academic research and scientific papers
Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin
Li, Jian,Hu, Qi-Long,Chen, Xue-Ping,Hou, Ke-Qiang,Chan, Albert S.C.,Xiong, Xiao-Feng
, p. 697 - 700 (2019/09/30)
An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.
Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes
Dong, Xiao-Yang,Du, Xuan-Yi,Fang, Jia-Heng,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Xin-Yuan,Wang, Li-Lei,Xia, Hai-Dong
, p. 16926 - 16932 (2020/08/25)
We describe a photoinduced copper-catalyzed asymmetric radical decarboxylative alkynylation of bench-stable N-hydroxyphthalimide(NHP)-type esters of racemic alkyl carboxylic acids with terminal alkynes, which provides a flexible platform for the construction of chiral C(sp3)?C(sp) bonds. Critical to the success of this process are not only the use of the copper catalyst as a dual photo- and cross-coupling catalyst but also tuning of the NHP-type esters to inhibit the facile homodimerization of the alkyl radical and terminal alkyne, respectively. Owing to the use of stable and easily available NHP-type esters, the reaction features a broader substrate scope compared with reactions using the alkyl halide counterparts, covering (hetero)benzyl-, allyl-, and aminocarbonyl-substituted carboxylic acid derivatives, and (hetero)aryl and alkyl as well as silyl alkynes, thus providing a vital complementary approach to the previously reported method.
OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS
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, (2018/07/29)
Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.
Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis
Moon, Patrick J.,Yin, Shengkang,Lundgren, Rylan J.
supporting information, p. 13826 - 13829 (2016/11/06)
We report decarboxylative carbonyl α-arylation by coupling of arylboron nucleophiles with malonic acid derivatives. This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing α-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.
N3-Arylmalonamides: A new series of thieno[3,2-b]pyridine based inhibitors of c-Met and VEGFR2 tyrosine kinases
Saavedra, Oscar,Claridge, Stephen,Zhan, Lijie,Raeppel, Franck,Granger, Marie-Claude,Raeppel, Stéphane,Mannion, Michael,Gaudette, Frédéric,Zhou, Nancy,Isakovic, Ljubomir,Bernstein, Naomy,Déziel, Robert,Nguyen, Hannah,Beaulieu, Normand,Beaulieu, Carole,Dupont, Isabelle,Wang, James,Macleod, A. Robert,Besterman, Jeffrey M.,Vaisburg, Arkadii
scheme or table, p. 6836 - 6839 (2010/06/19)
A family of thieno[3,2-b]pyridine based small molecule inhibitors of c-Met and VEGFR2 were designed based on lead structure 2. These compounds were shown to have IC50 values in the low nanomolar range in vitro and were efficacious in human tumo
Inhibitors of VEGF receptor and HGF receptor signaling
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Page/Page column 70-71, (2010/11/25)
The invention relates to the inhibition of VEGF receptor signaling and HGF receptor signaling. The invention provides compounds and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions
BACTERIOSTATIC HETEROCYCLES FROM EUODIA LUNU-ANKENDA
Manandhar, Mangala D.,Hussaini, Falak A.,Kapil, Randhir S.,Shoeb, Aboo
, p. 199 - 200 (2007/10/02)
A new constituent characterized as 8-acetyl-3,4-dihydroxy-5,7-dimethoxy-2,2-dimethylchroman has been isolated together with alloevodionol-7-methyl ether, 4-methoxy-1-methyl-2(1H) quinolinone, evolitrine, isoevodionol and its methyl ether from the aerial parts of Euodia lunu-ankenda.Its structure was confirmed by its transformation to alloevodionol-7-methyl ether. 4-Methoxy-1-methyl-2(1H)quinolinone and its isomer were synthesized by a modified procedure.Key Word Index - Euodia lunu-ankenda; Rutaceae; 8-acetyl-3,4-dihydroxy-5,7-dimethoxy-2,2-dimethylchroman; alloevodionol-7-methyl ether; 4-methoxy-1-methyl-2(1H)quinolinone; isoevodionol; isoevodionol methyl ether; antibacterial activity.
