58522-74-0Relevant academic research and scientific papers
Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates
Zhao, Hongyang,Xing, Yanpeng,Lu, Ping,Wang, Yanguang
, p. 15144 - 15150 (2016)
Cyclopenta[b]quinolines and cyclohexa[b]quinolines were prepared via the reactions of α-diazo ketones with N-(2-cyclopropylidenemethylphenyl)phosphanimines and N-(2-cyclobutylidenemethylphenyl) phosphanimine, respectively. The reaction proceeds in a cascade involving ketenimine formation, 6 π-electron ring closure, and 1,3-alkyl shift. A similar approach was developed for the synthesis of dihydropyrrolo-[2,3-b]quinolines from N-(2-cyclopropylidenemethylphenyl)phosphanimines and isocyanates.
Copper-Catalyzed Synthesis of 3-NO2 Quinolines from o-Azidobenzaldehyde and Nitro-olefins and its Application in the Concise Synthesis of Quindolines
Zheng, Lei,Zeng, Zhigang,Yan, Qiong,Jia, Fengcheng,Jia, Lihui,Chen, Yunfeng
supporting information, p. 4037 - 4042 (2018/09/14)
An efficient copper-catalyzed cyclization of o-azidobenzaldehyde and nitro-olefins was developed. This reaction proceeds under solvent-free conditions and displays broad functional group compatibility and affords 3-nitroquinolines in good to excellent yields. The synthetic utility of this strategy is illustrated by the concise construction of quindolines in only three steps, which renders the reaction more practical. (Figure presented.).
Photochemistry of ortho -Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control
Chaabouni,Pinkerton,Abid,Galaup,Chassaing
supporting information, p. 2614 - 2618 (2017/10/06)
The light-promoted potential of ortho -azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed towards different key heterocyclic scaffolds.
Synthesis of 2-nitroindoles via the Sundberg indole synthesis
Pelkey, Erin T.,Gribble, Gordon W.
, p. 5603 - 5606 (2007/10/03)
A three-step sequence has been developed for converting o-nitrobenzaldehydes into 2-nitroindoles. The key step involves the thermolysis of 2-(o-azidophenyl)nitroethylene (10) in xylenes which gives 2-nitroindole (4) in 54% yield, akin to the classic Sundberg indole synthesis. This procedure has also been utilized to synthesize 5,6-dimethoxy-2-nitroindole (14).
