26820-54-2Relevant articles and documents
Regioselective Alkylation of the Exocyclic Nitrogen of Heterocyclic Amidines via the Mitsunobu Reaction
Abarghaz, Mustapha,Kerbal, Abdelali,Bourguignon, Jean-Jacques
, p. 6463 - 6466 (1995)
Regioselective alkylation of heterocyclic amidines by means of Mitsunobu reaction leads to L-aminoacid derivatives.
ONSH: Optimization of oxidative alkylamination reactions through study of the reaction mechanism
Verbeeck, Stefan,Herrebout, Wouter A.,Gulevskaya, Anna V.,Van Der Veken, Benjamin J.,Maes, Bert U. W.
experimental part, p. 5126 - 5133 (2010/09/18)
(Figure presented) Oxidative alkylamination of electron-deficient (hetero)aromatic compounds, via the nucleophilic substitution of hydrogen, is a methodology that has made significant progress since the introduction of AgPy2MnO4 as oxidant. This oxidant generally gives good conversions and yields, whereas the use of KMnO4 only sometimes works equally well. In order to rationalize this, the reaction mechanism of oxidative alkylamination has been studied. 3-Nitropyridine (1), 1,3-dinitrobenzene (2), and quinazoline (3) were chosen as model substrates and n-butylamine and pyrrolidine as model alkylamines. The rate-limiting step of the mechanism for these substrate/alkylamine combinations was determined. With the use of 1H NMR spectroscopy thermodynamic properties of σ-- adduct formation were deduced and the effect of additives on the adduct formation was investigated. The fundamental insights resulting from these studies led to the identification of a cheap additive (tetrabutylammonium chloride), which in combination with the standard and cheap oxidant KMnO 4 generally gave excellent yields, similar to the ones previously obtained with more expensive AgPy2MnO4.
The effects of ring substituents and leaving groups on the kinetics of SNAr reactions of 1-halogeno- and 1-phenoxy-nitrobenzenes with aliphatic amines in acetonitrile
Crampton, Michael R.,Emokpae, Thomas A.,Isanbor, Chukwuemeka
, p. 1378 - 1383 (2008/09/18)
Rate constants are reported for the reactions of a series of 1-chloro-, 1-fluoro- and 1-phenoxy-nitrobenzenes activated by CF3 or CN groups or by ring-nitrogen with n-butylamine, pyrrolidine or piperidine in acetonitrile. The results are compar