905565-93-7Relevant academic research and scientific papers
Gold(iii)-catalyzed azide-yne cyclization/O-H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks
Bao, Ming,Huang, Jingjing,Qiu, Lihua,Su, Han,Xu, Xinfang,Zhang, Yuanqing
supporting information, p. 3888 - 3892 (2020/06/03)
A gold-catalyzed 6-endo-digazide-yne cyclization/O-H insertion cascade reaction of azide-tethered alkynes with alcohols has been developed, and it provides an expeditious access to 3-alkoxy-4-quinoline derivatives in good to high yields under mild and neutral reaction conditions with broad substrate generality. The utility of this method is emphasized by a scalable experiment and concise total synthesis of a bioactive natural product Leiokinine A, and other bioactive quinoline analogs.
Intramolecular pauson-khand reaction of alkyne-ketenimines and related [4+2] and [2+2] cycloadditions
Alajarin, Mateo,Ballester, Francisco-Jose,Vidal, Angel
, p. 418 - 424 (2018/05/22)
The first examples of intramolecular Pauson-Khand reactions involving ketenimines are reported. The alkyne-ketenimines participate through the C=C bond of the ketenimine fragment in the [2+2+1] cyclization process giving rise to cyclopenta[b]quinolin-2-ones. In the absence of metal carbonyl complexes, two competitive periselective cycloadditions occur when the alkyne-ketenimines are heated in benzene solution: a [4+2] process leading to benz[b]acridines as the major products, and a [2+2] route giving minor amounts of cyclobuta[b]quinolines.
A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl)benzene
Huo, Zhibao,Gridnev, Ilya D.,Yamamoto, Yoshinori
supporting information; experimental part, p. 1266 - 1270 (2010/04/29)
(Chemical Equation Presented) A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br 2 , ICl, NBS, NIS, and HNTf2) in CH3NO 2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, orH, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst. 2010 American Chemical Society.
A facile synthesis of pyrrolo[2,3-b]quinolines via a Rh(i)-catalyzed carbodiimide-Pauson-Khand-type reaction
Saito, Takao,Furukawa, Naoki,Otani, Takashi
supporting information; experimental part, p. 1126 - 1132 (2010/06/13)
A new straightforward synthetic method for 2,3-dihydro-1H-pyrrolo[2,3-b] quinolin-2-ones via a [RhCl(CO)2]2-dppp catalyzed Pauson-Khand-type reaction of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides is reported. The Royal Society of Chemis
Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates
Feldman, Ken S.,Iyer, Malliga R.,Hester II, D. Keith
, p. 3113 - 3116 (2007/10/03)
Thermolysis of 2-(allenyl)phenyl azides leads to a cascade cyclization sequence furnishing both C(2)-C(3) and N-C(2) cyclopentannelated indoles.
