Temperature switchable Brønsted acid-promoted selective syntheses of spiro-indolenines and quinolines

A high-yielding, temperature switchable divergent approach towards the synthesis of either spiro-indolenines or quinolines is described, starting from easily available indolyl ynones. The application of TFA at rt promotes the dearomatization of the indole, resulting in the formation of the spiro-indolenine, while at higher temperature, rearrangement results in the formation of the quinoline. © The Royal Society of Chemistry 2017.

Authors
Fedoseev P.1 , Van Der Eycken E.
Journal
Chemical Communications
Publisher
Royal Society of Chemistry
Number of issue
55
Language
English
Pages
7732-7735
Status
Published
Link
External link
DOI
10.1039/c7cc02580g
Volume
53
Year
2017
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 Peoples Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, Moscow, 117198, Russian Federation
Keywords
Bronsted acid; indole; quinoline derivative; spiro compound; aromatization; Article; diastereoisomer; high temperature; reaction time; synthesis; temperature
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/5917/
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