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Solvent-free Al(OTf)3-catalyzed aminolysis of 1,2-epoxides by 2-picolylamine: a key step in the synthesis of ionic liquids



Solvent-free Al(OTf)3-catalyzed aminolysis of 1,2-epoxides by 2-picolylamine: a key step in the synthesis of ionic liquids



Journal of Organic Chemistry 69(22): 7745-7747



Beta-Amino alcohols N-2'-pyridylmethyl substituted 3 have been prepared in excellent yields under mild conditions by the first Lewis acid-catalyzed aminolysis of 1,2-epoxides 1 with the bihaptic amine 2-picolylamine (2) with use of 5 mol % of Al(OTf)(3) under solvent-free conditions. As a representative of a new class of ionic liquids, cis-5-[(4'-methylphenyl)sulfonyl]-1,2,3,4,4a,5,6,11a-octahydropyrido[1,2-a]quinoxalin-11-ium methanesulfonate (6) and its chloride derivative 7 have been synthesized under environmentally friendly conditions by the one-pot aminolysis of cyclohexene oxide (1a) with 2 and intramolecular cyclization of the resulting 2-[(pyridin-2'-yl)methylamino]cyclohexanol (3a).

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Accession: 050337631

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PMID: 15498007

DOI: 10.1021/jo049335f


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