Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates.
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.
Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China.
Hongyang
H
Zhao
Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China.
Yanpeng
Y
Xing
Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China. pinglu@zju.edu.cn.
Ping
P
Lu
Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China. orgwyg@zju.edu.cn.
Yanguang
Y
Wang
D002234:Carbodiimides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D017953:Isocyanates / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D002234:Carbodiimides; D007097:Imines; D017953:Isocyanates; D009570:Nitriles; D011804:Quinolines; C000591102:ketenimine
carbodiimides; heterocycles; ketenimines; quinoline synthesis; quinolines