33901-53-0Relevant articles and documents
Nucleophilic substitution on 4-hydroxymethylanilines under 'neutral' conditions via aza quinone methide intermediate
Takahashi, Hiroyasu,Kashiwa, Nobuyuki,Kobayashi, Hisayoshi,Hashimoto, Yuichi,Nagasawa, Kazuo
, p. 5751 - 5753 (2002)
Substitution reaction of 4-hydroxymethylaniline derivatives with resonance-stabilized carbon nucleophiles and an acid-labile nucleophile, including β-ketoester, 1,3-diketone, α-nitroester, and silylenolether, proceeded efficiently upon heating at 80°C in a neutral solvent system. The reaction was successfully applied to the synthesis of 4-aminophenylalanine.
Catalyst-Free [3 + 3] Annulation/Oxidation of Cyclic Amidines with Activated Olefins: When the Substrate Olefin Is Also an Oxidant
Han, Wendan,Li, Yuanhang,Raveendra Babu, Kaki,Li, Jing,Tang, Yuhai,Wu, Yong,Xu, Silong
, p. 7832 - 7841 (2021/06/25)
Herein we describe a catalyst-free regioselective [3 + 3] annulation/oxidation reaction of cyclic amidines such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) and DBN (1,5-diazabicyclo(4.3.0)non-5-ene) with activated olefins, i.e., 2-arylidenemalononitriles and 2-cyano-3-aryl acrylates, to afford tricyclic 2-pyridones and pyridin-2(1H)-imines, respectively. The mechanism has been proposed based on DFT calculations. In the reaction, the cyclic amidines serve as C,N-bisnucleophiles for the cyclization, while the olefins play a dual role by acting as both reactants and oxidants.
Monosubstituted malononitriles: Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes
Tayyari, Fariba,Wood, Dwight E.,Fanwick, Phillip E.,Sammelson, Robert E.
, p. 279 - 285 (2008/12/22)
A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Inco
