1341221-03-1Relevant articles and documents
Povarov-type reaction using methyl as new input: Direct synthesis of substituted quinolines by I2-mediated formal [3 + 2 + 1] cycloaddition
Gao, Qinghe,Liu, Shan,Wu, Xia,Wu, Anxin
, p. 4582 - 4585 (2014)
A highly efficient molecular iodine mediated formal [3 + 2 + 1] cycloaddition reaction for the direct synthesis of substituted quinolines from methyl ketones, arylamines, and styrenes is developed. The methyl group of the methyl ketone represents uniquely reactive input in the Povarov reaction. A self-sequenced iodination/Kornblum oxidation/Povarov/aromatization mechanism has been proposed as a possible reaction sequence to account for the results observed in this study.
RuII-Catalyzed/NH2-Assisted Selective Alkenyl C-H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines
Chen, Pu,Nan, Jiang,Hu, Yan,Ma, Qiong,Ma, Yangmin
, p. 4812 - 4815 (2019)
A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly of highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C-H activation with sulfoxonium ylides as one-carbon coupling partners. Various 2-acylquinolines could be obtained with good yields and excellent functional group tolerance. Moreover, the potential synthetic application of this methodology was exemplified by several chemical transformations.
Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine
Liu, Luyao,Lin, Jingyang,Pang, Mingxuan,Jin, Huile,Yu, Xiaochun,Wang, Shun
, p. 1146 - 1151 (2022/02/14)
A novel photo-thermo-mechanochemical approach to assembling quinolines catalyzed by iron(II) phthalocyanine has been realized for the first time. This transformation features a cost-efficient catalytic system and operational simplicity, is free of solvent, and shows good substrate tolerance, providing a green alternative to existing thermal approaches. Mechanistic experiments demonstrate that the in-situ-formed secondary amine may be the key intermediate for the further cyclization/aromatization process.
Employing Arylacetylene as a Diene Precursor and Dienophile: Synthesis of Quinoline via the Povarov Reaction
Yu, Xiao-Xiao,Zhao, Peng,Zhou, You,Huang, Chun,Wang, Li-Sheng,Wu, Yan-Dong,Wu, An-Xin
, p. 8381 - 8388 (2021/06/30)
A novel I2-mediated Povarov reaction of arylacetylenes and anilines for the synthesis of 2,4-substituted quinolines has been developed, in which arylacetylene first acts as both a diene precursor and dienophile. This work further develops the Povarov reaction to expand the types of diene precursors. Preliminary mechanistic studies indicate that the I2/DMSO system realized the oxidative carbonylation of C(sp)-H of arylacetylene and then undergoes a [4 + 2] cycloaddition reaction.
Coproduct promoted povarov reaction: Synthesis of substituted quinolines from methyl ketones, arylamines, and α-ketoesters
Gao, Qinghe,Liu, Shan,Wu, Xia,Zhang, Jingjing,Wu, Anxin
, p. 5984 - 5991 (2015/06/16)
A highly efficient I2-catalyzed Povarov-type reaction of methyl ketones, arylamines, and α-ketoesters is developed. This reaction utilizes a catalytic amount of HI coproduct as a promoter for the synthesis of substituted quinolones. This simple procedure represents an interesting new form of reactivity for the Povarov reaction with good functional group compatibility.
Iron-catalyzed oxidative tandem reactions with TEMPO oxoammonium salts: Synthesis of dihydroquinazolines and quinolines
Rohlmann, Renate,Stopka, Tobias,Richter, Heinrich,Garcia Mancheno, Olga
, p. 6050 - 6064 (2013/07/26)
A straightforward iron-catalyzed divergent oxidative tandem synthesis of dihydroquinazolines and quinolines from N-alkylanilines using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has been developed. Fe(OTf) 2 was the Lewis acid cata
TEMPO oxoammonium salt-mediated dehydrogenative Povarov/oxidation tandem reaction of N-alkyl anilines
Richter, Heinrich,Garcia Mancheno, Olga
supporting information; experimental part, p. 6066 - 6069 (2012/01/13)
The synthesis of a variety of substituted quinolines from N-alkyl anilines by a one-pot dehydrogenative Povarov/oxidation tandem reaction with mono- and 1,2-disubstituted aryl and alkyl olefins was developed. A simple protocol using cheap and benign iron(
