Simple One-Pot Synthesis of New Derivatives of the Macrocyclic Aminal 1,3,7,9,13,15,19,21-Octaazapentacyclo-[19.3.1.1^3,7.1^9,13.1^15,19]octacosane (OAPO)

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-octaazapentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]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.

GRAPHICAL ABSTRACT

Keywords:

• Anomeric effect
• hexahydropyrimidine
• Mannich bases
• ortho-regioselectivity

ACKNOWLEDGMENTS

We acknowledge the Dirección de Investigaciones Sede Bogotá (DIB) of Universidad Nacional de Colombia for financial support, and D. M. G. acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.