4,4′-substituted-2,2′-((hexahydro-1
H-benzo[
d]imidazole-1,3(2
H)-diyl)
bis(methylene))
bisphenols (
1a–
d) and 2,6-
bis{[3-(2-hydroxy-5-substitutedbenzyl)octahydro-1
H-benzimidazol-1-yl]methyl}-4-substitutedphenols (
2a–
b) were synthesized via microwave (MW) irradiation of aminal (2
R,7
R,11
S,16
S
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4,4′-substituted-2,2′-((hexahydro-1
H-benzo[
d]imidazole-1,3(2
H)-diyl)
bis(methylene))
bisphenols (
1a–
d) and 2,6-
bis{[3-(2-hydroxy-5-substitutedbenzyl)octahydro-1
H-benzimidazol-1-yl]methyl}-4-substitutedphenols (
2a–
b) were synthesized via microwave (MW) irradiation of aminal (2
R,7
R,11
S,16
S)-1,8,10,17-tetraazapentacyclo[8.8.1.1.
8,170.
2,70.
11,16]icosane
2 with
p-substituted phenols. Microwave (MW) irradiation improved reaction rates and yields at 80 °C. Compounds
1a–
d were racemic, and
2a–
b were diastereomeric. NMR spectra revealed key signals for the perhydrobenzimidazole fragment, aromatic rings, and aminal carbons. Differences in the
13C NMR spectra highlighted structural variations, such as distinct carbonyl and methoxyl signals in
2d. MW irradiation at higher temperatures (100–120 °C) reduced yields of
1, especially for phenols with methyl (Me) and methoxy (OMe) groups, suggesting a shift toward the formation of compound
2. Additionally, higher temperatures led to polymerization byproducts, emphasizing the impact of MW energy on reaction pathways. These results provide valuable insights for designing molecules with potential applications in materials science and medicinal chemistry.
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