180597-81-3Relevant articles and documents
[Omim][Bf4] ionic liquid, a green and recyclable medium for one-pot aminomethylation of electron-rich aromatic compounds
Arzephoni, Amene Yaghoubi,Naimi-Jamal, M. Reza,Sharifi, Ali,Abaee, M. Saeed,Mirzaei, Mojtaba
, p. 216 - 218 (2013)
An efficient catalyst-free procedure has been developed for one-pot aminomethylation of some electron-rich aromatic compounds such as 1- and 2-naphthols, indole, N-methylindol and benzamide, in [omim][BF4] ionic liquid at room temperature. The ionic liquid can be recovered and reused without any noticeable loss of performance.
Efficient and practical synthesis of Mannich bases related to gramine mediated by zinc chloride
Dai, Hong-Guang,Li, Ji-Tai,Li, Tong-Shuang
, p. 1829 - 1835 (2007/10/03)
An efficient and practical procedure for the Mannich reaction of secondary amine, formaldehyde, and indole or N-methylindole employing zinc chloride is presented. A series of gramine derivatives were obtained in 58-98% yields at room temperature in EtOH by using this method. Copyright Taylor & Francis Group, LLC.
Solvent-free aminoalkylation of phenols and indoles assisted by microwave irradiation
Sharifi,Mirzaei,Naimi-Jamal
, p. 875 - 880 (2007/10/03)
Phenols and indoles were aminoalkylated in a solvent-free and environmentally friendly Mannich reaction on acidic alumina assisted by microwave irradiation in good overall yields.
The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles
Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 2941 - 2958 (2007/10/03)
Dichlorodimethylsilane and trichloromethylsilane have been used to generate iminium ions from aminals and aminol ethers derived from secondary alkylamines, including glycine derivatives, in aprotic media which were shown to undergo reactions with electron rich aromatic heterocycles, including furan, to give mono-aminoalkylation products in good yields. Whereas chlorotrimethylsilane has been shown to generate iminium ions from aminol ethers, no evidence was adduced for the involvement of iminium ions using aminals. 2,5-Disubstitution of N-methylpyrrole was the major result in reactions of N-methylpyrrole with aminals in the presence of chlorotrimethylsilane where no build up of hydrogen chloride occurs and where chlorotrimethylsilane can function catalytically. Experimental results, including the use of bis(trimethylsilyl)acetamide as a proton scavenger, and some relative rate data, are presented that allow possible mechanisms to be evaluated.
