Functionalized macrocycles from functionalized tetra-amines: pendent-arm macrocycles derived from dichloropivalic acid.
Paul V Bernhardt, Jack M Harrowfield, Yang Kim, George A Koutsantonis, Young Hoon Lee, Pierre Thuéry
文献索引:Inorg. Chem. 43(5) , 1681-8, (2004)
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摘要
Reaction between ethane-1,2-diamine and 3,3'-dichloropivalic acid results in different, isomeric tetra-amine derivatives, one a tetraamino carboxylic acid and the other a carboxamidotriamino alcohol, depending upon reaction conditions. Intended conversion of the Cu(II) complex of the former to a cyclam-like macrocycle through reaction with nitroethane and formaldehyde results in isolation of derivatives of both the former and the latter. This can be rationalized by assuming the intermediacy of an azetidinone, a species similar to that seen in simpler reactions of dichloropivalates. A single reaction thereby provides pendent-arm macrocycles where one has an electrophilic and the other a nucleophilic substituent. Parallel chemistry is not seen in the reaction between propane-1,3-diamine and 3,3'-dichloropivalate.
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A novel rearrangement reaction conversion of 3-(chloromethyl) azetidin-2-ones to azetidine-3-carboxylic acid esters. Bartholomew D and Stocks MJ.
[Tetrahedron Lett. 32(36) , 4795-98, (1991)]