N-Benzylazacyclophane synthesis via aromatic Mannich reaction |
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Authors: | Christian Dí az-Oviedo,Rodolfo Quevedo |
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Affiliation: | Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra. 30 No. 45-03, Bogotá, Colombia |
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Abstract: | A new method for synthesizing phenolic N-benzylazacyclophanes starting from tyramine is presented here. Computational calculations showed that macrocyclization is favored by the formation of hydrogen bond-based templates; these templates are not affected by including benzyl groups in the nitrogen atom of the tyramine moiety. The results showed that N-benzyl groups with electron-donating substituents have more nucleophilic nitrogen atoms, thereby favoring macrocyclization, while electron-withdrawing groups favor polymerization. |
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Keywords: | Tyramine Cyclophane Mannich reaction Formaldehyde Phenol |
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