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Table 4 Assignment of the 1 H NMR spectra of compounds 8a-l

From: Single-step synthesis of a new series of meso di-Mannich bases from the cyclic aminal (2S,7R,11S,16R)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,7011,16]icosane and p-substituted phenols

Product R Ar-OH H-5. H-3, H-6, H-2, ArCH2N H-3a, H-4, H-5
    H-5′ H-3′ H-6′ H-2′   H7a H-6, H-7
8a F 10.34, bs 6.87, td, J = 8.0 Hz, J = 8.2 Hz, J = 3.1 Hz 6.70, dd, J = 8.0 Hz, J = 2.8 Hz 6.76, dd, J = 8.0 Hz, J = 4.8 Hz 3.39,d, 3.84, d, J = 6.4 Hz 3.63, d, 4.03, d, J = 14.0 Hz 3.11, t, J = 4.0 Hz 1.30-1.80, m
8b Cl 10.63, bs 7.15, dd, J = 8.6 Hz, J = 2.6 Hz 6.97, d, J = 2.5 Hz 6.78, d, J = 8.6 Hz 3.39, d, 3.85, d J = 6.6 Hz 3.64, d, 4.04, d J = 14.0 Hz 3.11, t, J = 4.1 Hz 1.30-1.80, m
8c Br 10.55, bs 7.26, dd, J = 8.6 Hz, J = 2.4 Hz 7.09, d, J = 2.4 Hz 6.72, d, J = 8.6 Hz 3.36, d, 3.84, d J = 6.6 Hz 3.62, d, 4.02, d, J = 13.9 Hz 3.09, t, J = 4.0 Hz 1.30-1.80, m
8d I --- 7.45, d, J = 8.8 Hz 7.27, s 6.62, d, J = 8.5 Hz 3.62, d, 3.85, d, J = 8.0 Hz 3.62, d, 4.01, d, J = 13.9 Hz 3.11, t, J = 4.0 Hz 1.30-1.80, m
8e (C = O)OMe (3.87, s) 10.79, bs 7.96, dd, J = 8.4 Hz, J = 2.1 Hz 7.74, d, J = 2.1 Hz 6.87, d, J = 8.8 Hz 3.42, d, 3.85, d, J = 8.0 Hz 3.67, d, 4.06, d, J = 14.0 Hz 3.11, t, J = 4.0 Hz 1.30-1.80, m
8f (C = O)OEt (1,35, t; 4,31, q) ---- 7.88, dd, J = 8.5 Hz, J = 2.1 Hz 7.70, d, J = 2.0 Hz 6.83, d, J = 8.5 Hz 3.37, d, 3.86, d, J = 6.6 Hz 3.72, d, 4.09, d, J = 13.9 Hz 3.11, t, J = 4.0 Hz 1.30-1.80, m
8 g (C = O)OPr (1.01, t; 1.75, m; 4.22, t) ---- 7.89, dd, J = 8.5 Hz J = 2.1 Hz 7.71, d, J = 1.9 Hz 6.86, d, J = 8.5 Hz 3.44, d, 3.91, d, J = 6.2 Hz 3.75, d, 4.10, d, J = 13.8 Hz 3.15, t, J = 4.0 Hz 1.30-1.80, m
8 h (C = O)OBu (0.96, m; 1.44, m; 1.71, qn; 4.26, t) ---- 7.88, dd, J = 8.5 Hz, J = 2.1 Hz 7.69, d, J = 2.1 Hz 6.83, d, J = 8.5 Hz 3.36, d, 3.85, d, J = 6.6 Hz 3.72, d, 4.09, d, J = 13.9 Hz 3.10, t, J = 4.0 Hz 1.30-1.80, m
8i H (6.77, td) 10.60, bs 7.17, dd, J = 8.0 Hz J = 1.2 Hz 6.96, d, J = 7.2 Hz 6.82, dd, J = 8.1 Hz, J = 1.0 Hz 3.42, d 3.84, d, J = 6.6 Hz 3.67, d, 4,06, d, J = 13.8 Hz 3.11, t, J = 4.0 Hz 1.30-1.80, m
8j Me (2.24, s) 10.62, bs 6.99, d, J = 8.2 Hz 6.79, s 6.74, d, J = 8.2 Hz 3.44, d 3.83, d, J = 6.5 Hz 3.64, d, 4.04, d, J = 13.7 Hz 3.12, t, J = 4.1 Hz 1.30-1.80, m
8 k t-Bu (1.27, s) 10.62, bs 7.19, dd, J = 8.5 Hz, J = 2.4 Hz 6.96, d, J = 2.4 Hz 6.75, d, J = 8.5 Hz 3.47, d 3.86, d, J = 6.6 Hz 3.67, d 4.07, d, J = 13.8 Hz 3,11, t, J = 4.3 Hz 1.30-1.80, m
8 l OMe (3.71, s) 10.15, bs 6.73, d, J = 8.8 Hz 6.53, d, J = 2.0 Hz 6.75, d, J = 8.8 Hz 3.42, d 3.83, d, J = 6.5 Hz 3.62, d 4.02, d, J = 13.7 Hz 3,11, t, J = 4.1 Hz 1.30-1.80, m
  1. Table 4 shows all the measured signals for hydrogen atoms in compounds 8a-l in the 1H NMR spectra and their assignation in the molecular structure.