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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.