A new approach towards 2-amino-1-aryloxy-3-methoxypropanes from 1-arylmethyl-2-(bromomethyl)aziridines |
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Authors: | Matthias D'hooghe |
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Institution: | Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium |
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Abstract: | 1-Arylmethyl-2-(bromomethyl)azirdines were converted into the corresponding 2-(aryloxymethyl)aziridines upon treatment with the appropriate potassium phenoxides in DMF/acetone in excellent yields, followed by regioselective ring opening towards N,N-di(arylmethyl)-N-(2-bromo-3-aryloxypropyl)amines using benzyl bromide in acetonitrile. Treatment of the latter β-bromoamines with sodium methoxide afforded the desired 2-amino-1-aryloxy-3-methoxypropanes as the major compounds (49-58%) besides the isomeric 3-amino-1-aryloxy-2-methoxypropanes in minor quantities (9-15%). |
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Keywords: | 2-(Bromomethyl)aziridines 2-Amino-3-alkoxy-1-aryloxypropanes Substitution Ring opening Aziridinium salts |
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