16619-52-6Relevant academic research and scientific papers
A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines
Lázaro-Milla, Carlos,Almendros, Pedro
, p. 13534 - 13538 (2021/08/13)
We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.
Gold(i) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines
Sun, Yuan-Ming,Gu, Peng,Gao, Yu-Ning,Xu, Qin,Shi, Min
, p. 6942 - 6945 (2016/06/06)
An effective synthetic protocol for structurally diverse 4-acyloxy-1,2-dihydroquinoline compounds has been accomplished by a gold(i)-catalyzed tandem [3,3]-rearrangement and intramolecular hydroamination of propargylic esters, affording the desired products in good yields. Moreover, the asymmetric variant of this cyclization has also been achieved using a chiral nitrogen acyclic carbene (NAC) gold(i) complex. These products have application in the enantioselective synthesis of an aromatase inhibitor within three simple steps.
Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach
Saito, Kodai,Moriya, Yuka,Akiyama, Takahiko
, p. 3202 - 3205 (2015/07/15)
Chiral 2-substituted 2,3-dihydro-4-quinolones were synthesized based on the chiral phosphoric acid catalyzed intramolecular aza-Michael addition reaction using N-unprotected 2-aminophenyl vinyl ketones as substrates in good yields with high enantioselectivities. (Chemical Equation Presented).
Enantioselective synthesis of azaflavanones using organocatalytic 6-endo aza-Michael addition
Cheng, Shuanghua,Zhao, Lili,Yu, Shouyun
, p. 982 - 986 (2014/04/03)
A method to prepare highly enantioenriched azaflavanones using an organocatalytic 6-endo aza-Michael addition has been described. A variety of 2-aryl-, 2-vinyl- and 2-methylazaflavanones were prepared in good yields (53-84%) and excellent enantioselectivities (97.6:2.4 to 99.3:0.7 er).
Design and synthesis of aza-flavones as a new class of xanthine oxidase inhibitors
Dhiman, Rajni,Sharma, Sahil,Singh, Gagandip,Nepali, Kunal,Singh Bedi, Preet Mohinder
, p. 7 - 16 (2013/02/23)
In an attempt to develop non-purine-based xanthine oxidase (XO) inhibitors, keeping in view the complications reported with the use of purine-based XO inhibitors, the flavone framework (a class possessing XO inhibitory potential) was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone (a bicyclic unit present in flavones), owing to the bioactive potential and drug-like properties of quinolones. This type of replacement does not alter the shape and structural features required for XO inhibition, and also provides some additional interaction sites, without the loss of hydrogen bonding and hydrophobic and arene-arene interactions. In the present study, a series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was rationally designed, synthesized and evaluated for in vitro XO inhibitory activity. Some notions about structure-activity relationships are presented indicating the influence of the nature of the 2-aryl ring on the inhibitory activity. Important interactions of the most active compound 3l (IC50 = 6.24 μM) with the amino acid residues of the active site of XO were figured out by molecular modeling. To develop non-purine-based xanthine oxidase inhibitors, the flavone framework was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone. This type of replacement does not alter the shape and structural features required for xanthine oxidase inhibition. The rationally designed and synthesized series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was evaluated for in vitro xanthine oxidase inhibitory activity. Copyright
ZnCl2-catalyzed intramolecular cyclization reaction of 2-aminochalcones using polymer-supported selenium reagent: Synthesis of 2-phenyl-4-quinolones and 2-phenyl-2,3-dihydroquinolin-4(1 H)-one
Tang,Chen, Bangzheng,Zhang, Lianpeng,Li, Wen,Lin, Jun
scheme or table, p. 707 - 711 (2011/04/26)
A new and efficient method for the synthesis of 2-phenyl-4-quinolones and 2-phenyl-2,3-dihydroquinolin-4(1H)-ones is described. The reaction involves ZnCl2-mediated polystyrene-supported selenium-induced intramolecular cyclization of 2-amino-chalcones and subsequent traceless or functionalizing cleavage of selenium linker. Georg Thieme Verlag Stuttgart - New York.
Synthesis of Isocoumarin, 1-Isoquinolone and 4(1H)-Quinolone Derivatives via Seleno-intermediates
Izumi, Taeko,Morishita, Nobuya
, p. 145 - 152 (2007/10/02)
The reaction of 2-styrylbenzoic acid 2 with N-phenylselenosuccinimide (N-PPS) affords 3-phenyl-iso-coumarin derivatives 3 and 3,4-dihydro-3-phenyl-4-(phenylseleno)isocoumarins 4 via selenolactonization.The reaction of 2-styrylbenzamides 5 and 1-(2-aminoph
