80865-94-7Relevant academic research and scientific papers
Direct: N -alkylation of sulfur-containing amines
Li, Chen,Ge, Min-Tong,Bai, Liang,Xia, Ai-Bao,Xu, Dan-Qian,Xu, Zhen-Yuan
supporting information, p. 4478 - 4482 (2021/05/31)
An efficient ruthenium-catalyzed method has been developed for the direct N-alkylation of sulfur-containing amines with alcohols, for the first time, by a step-economical and environmentally friendly hydrogen borrowing strategy. The present methodology features base-free conditions and broad substrate scope, with water being the only by-product. Moreover, this protocol has been applied to the synthesis of the pharmaceutical drug Quetiapine.
N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 3210 - 3215 (2007/10/02)
The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 deg C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents , (EtO)2CO, CH2=CHCO2Me, , PhCH=NPh, MeI, and CH2=CHCH2Br> to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5.When the reductive opening and the reaction with electrophiles were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with the same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.
Naphthalene-Catalysed Reductive Opening of Aziridines with Lithium: A Direct Preparation of N-Lithio-2-lithioalkylamines
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 1649 - 1652 (2007/10/02)
The reductive opening of N-phenylaziridine (1) with an excess of lithium powder in the presence of a catalytic amount (5 molar percent) of naphthalene at -78 deg C leads to the corresponding N-lithio-2-lithioethylamine (2), which by reaction with different electrophiles (water, deuterium oxide, dimethyl disulphide, pivalaldehyde or cyclohexanone) affords the expected products 3.The same process applied to N-cyclohexylaziridine fails.The reaction also works with the chiral aziridine 4 yielding the chiral deuteriated amine 5, through the corresponding chiral dianionic intermediate.
β-Substituted Organolithium Compounds. Reaction with Alkyl Halides, Dimethyl Disulfide, and Imines
Barluenga, Jose,Fananas, Francisco J.,Villamana, Jorge,Yus, Miguel
, p. 1560 - 1564 (2007/10/02)
The reaction of β-substituted organolithium derivatives with several electrophiles leads to mono- as well as bifunctionalized organic compounds.Thus, by treatment of these dianions with alkyl halides a direct attack on the carbanionic carbon atom is performed, giving as a result substituted amines.When dimethyl disulfide is used, β-amino and β-hydroxy thioethers are obtained.Finally, on reaction with imines, 1-amino-3-hydroxy compounds and 1,3-diamines are obtained.Since these dianions are easily preparated by mercury-lithium transmetalation from β-substituted organomercurials resulting from the addition of mercury(II) salts to olefins, this whole process gives an appropriate way of functionalizing olefins.
