Reactions of 2-hydroxy-5-(1-adamantyl)benzene-1,3-dicarbaldehyde with ethane-1,2-diamine, trans-cyclohexane-1,2-diamine, and N-(2-aminoethyl)ethane-1,2-diamine

Reactions of 2-hydroxy-5-(1-admantyl)benzene-1,3-dicarbaldehyde with ethane-1,2-diamine, transcyclohexane-1,2-diamine, and N-(2-aminoethyl)ethane-1,2-diamine were studied in strongly dilute solution and under conditions of template synthesis in the presence of H3BO3. The effects of reaction conditions and initial diamine structure on the cyclocondensation process were determined. Selective [3 + 3]-cyclocondensation of 2-hydroxy-5-(1-admantyl)benzene-1,3-dicarbaldehyde with trans-cyclohexane-1,2-diamine and [2 + 2]-cyclization with N-(2-aminoethyl)ethane-1,2-diamine were performed in chloroform in the presence of H3BO3. The first representative of adamantylcalixsalens was synthesized.