Simple One-Pot Synthesis of New Derivatives of the Macrocyclic Aminal 1,3,7,9,13,15,19,21-Octaazapentacyclo-[19.3.1.13,7.19,13.115,19]octacosane (OAPO) |
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Authors: | Augusto Rivera Jaime Ríos-Motta Ginna Paola Trujillo Derly Marcela González Daniel Alcázar |
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Institution: | 1. Departamento de Química , Universidad Nacional de Colombia, Ciudad Universitaria , Bogotá , Colombia ariverau@unal.edu.co;3. Departamento de Química , Universidad Nacional de Colombia, Ciudad Universitaria , Bogotá , Colombia |
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Abstract: | A series of 2,2′-(dihydropyrimidine-1,3(2H,4H)-diyldimethanediyl)bis(substituted-phenols) was synthesized using a Mannich-type reaction between the macrocyclic aminal 1,3,7,9,13,15,19,21-octaazapentacyclo19.3.1.13,7.19,13.115,19]octacosane (OAPO) (1) and substituted phenols in basic media. These previously unreported compounds were separated from the reaction mixture by column chromatography in highly pure form with 25–75% yields. The most stable conformer was predicted using AM1-type semiempirical quantum chemical calculations. |
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Keywords: | Anomeric effect hexahydropyrimidine Mannich bases ortho-regioselectivity |
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