23562-77-8Relevant academic research and scientific papers
Convenient synthesis of 2-Amino-4H-chromenes from photochemically generated o-quinone methides and malononitrile
Fujiwara, Makoto,Sakamoto, Masanori,Komeyama, Kimihiro,Yoshida, Hiroto,Takaki, Ken
, p. 59 - 66 (2015/01/30)
2-Amino-4H-chromenes were synthesized in moderate to good yields by the reaction of o-quinone methides photochemically generated from o-(dimethylaminomethyl)phenols with malononitrile. This method was applicable to the synthesis of fluorinated chromenes that were difficult to obtain by other methods. In addition, o-(hydroxymethyl)phenols could be used for the reaction in the presence of tertiary amine bases.
Metalation of Phenols. Synthesis of Benzoquinones by the Oxidative Degradation Approach
Saa, Jose M.,Llobera, Antonia,Garcia-Raso, Angel,Costa, Antonio,Deya, Pedro M.
, p. 4263 - 4273 (2007/10/02)
In a effort to explore the potential of so-called oxidative degradation approach for the synthesis of quinones, we have investigated the direct metalation of a number of simple phenols such as o- and p-hydroxybenzyl alcohols, benzyl methyl ethers and N,N-dimethylbenzylamines.Apparently, only those phenolic substrates having available both a coordinating group for chelation and an electron-withdrawing group in a 1,3-relationship are efficiently lithiated, by the action of n-BuLi, in a regioselective manner.Those positions on the aromatic nucleus just flanked by a coordinating, or an acid-base, group could be metalated by action of the t-BuLi/THP system, in favorable cases.
