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Divergent Synthesis of Quinoline Derivatives via [5+1] Annulation of 2‐Isocyanochalcones with Nitroalkanes
Author(s) -
Bao Lan,
Liu Jinglin,
Xu Liang,
Hu Zhongyan,
Xu Xianxiu
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800152
Subject(s) - annulation , chemistry , quinoline , nitro , substrate (aquarium) , combinatorial chemistry , tricyclic , transformation (genetics) , organic chemistry , stereochemistry , catalysis , biochemistry , alkyl , oceanography , gene , geology
An unprecedented substrate‐dependent [5+1] annulation of 2‐isocyanochalcones with nitroalkanes was developed for the efficient synthesis of functionalized quinolines and 3‐nitrodihydroquinolines. This transformation delivers both the aromatic and dihydroquinolines by selectively elimination or retention of the nitro group. Moreover, 3‐nitroquinolines and tricyclic pyrrolo[2,3‐ c ]quinolines were conveniently constructed from the resulting 3‐nitrodihydroquinolines through a single operation, respectively.