Acylimines of MTFP and C,Nꢀbisnucleophiles
Russ.Chem.Bull., Int.Ed., Vol. 54, No. 12, December, 2005 2855
Table 2. 1H and 19F NMR spectra of compounds 4a—h, 10a—g, 11a—e, 12a—c, 13a—e, 14a,b, and 16
Comꢀ
pound
δ (J/Hz)
1H
19F
4a
2.43 (s, 3 H, Me); 2.81, 3.43 (both s, 3 H each, MeN); 7.17, 7.55 (both d, 2 H each, CHAr, J = 8.1);
9.38, 11.01, 12.25 (all s, 1 H each, NH)
4.78 (s)
4b
4c
1.98 (s, 3 H, Me); 7.34 (m, 2 H, CHAr); 7.53 (m, 3 H, CHAr); 9.45, 11.07, 11.28 (all s, 1 H each, NH)
1.96 (s, 3 H, Me); 7.21—7.42 (m, 4 H, CHAr); 9.45, 11.07, 11.28 (all s, 1 H each, NH)
4.09 (s)
–33.67 (m, 1 F);
4.10 (s, 3 F)
4.13 (s)
4d
0.96 (d, 6 H, Me, J = 7.9); 2.08 (m, 3 H, CH2 + CH); 7.33 (m, 2 H, CHAr); 7.58 (m, 3 H, CHAr);
9.31, 11.05, 11.08 (all s, 1 H each, NH)
4e
7.12, 7.32, 7.48 (all m, 2 H each, CHAr); 7.63 (t, 2 H, CHAr, J = 7.6);
9.59, 11.24, 11.49 (all s, 1 H each, NH)
–34.95 (m, 1 F);
4.15 (s, 3 F)
4f
7.21 (t, 2 H, CHAr, J = 7.5); 7.33 (m, 3 Н, CHAr); 7.52, 8.04 (both m, 2 H each, CHAr);
9.79, 11.08, 11.34 (all s, 1 H each, NH)
–30.08 (m, 1 F);
4.75 (s, 3 F)
4g
2.98, 4.22 (both m, 2 H each, CH2); 7.08—7.38 (m, 7 Н, CHAr); 8.01 (t, 2 Н, CHAr, J = 7.8);
9.89, 10.92, 12.12 (all s, 1 H each, NH)
–29.75 (m, 1 F);
4.73 (s, 3 F)
4h
6.52 (m, 1 H, CHFur); 7.35 (m, 3 Н, CHAr + CHFur); 7.53 (m, 3 Н, CHAr); 8.72 (m, 1 H, CHFur);
9.45, 11.18, 11.42 (all s, 1 H each, NH)
4.59 (s)
10a
10b
10c
10d
10e
10f
5.21 (m, 1 H, H2C=); 5.36 (m, 3 H, CH2N + CH=); 5.98 (m, 1 H, H2C=); 7.55 (m, 3 H, CHAr);
7.98 (d, 2 H, CHAr, J = 7.4); 9.78, 11.96, 12.09 (all s, 1 H each, NH)
1.86 (s, 3 H, Me); 4.63 (m, 1 H, H2C=); 4.92 (m, 3 H, CH2N + H2C=); 7.47 (m, 3 H, CHAr);
7.93 (m, 2 H, CHAr); 9.91, 12.10, 12.42 (all s, 1 H each, NH)
1.82 (s, 3 H, Me); 4.85 (m, 4 H, CH2N + H2C=); 7.21 (m, 2 H, CHAr); 7.47, 7.61 (both m,
1 H each, CHAr); 9.66, 12.10, 12.41 (all s, 1 H each, NH)
2.41 (s, 3 Н, Ме); 7.23 (d, 2 Н, CHAr, J = 8.2); 7.36 (m, 2 Н, CHAr); 7.54 (m, 3 Н, CHAr);
7.84 (d, 2 Н, CHAr, J = 8.2); 9.71, 11.13, 11.39 (all s, 1 H each, NH)
5.64 (s, 2 H, CH2); 7.15—7.58 (m, 7 Н, CHAr); 8.05 (t, 2 Н, CHAr, J = 7.8);
9.99, 12.31, 12.48 (all s, 1 H each, NH)
5.66 (s, 2 H, CH2); 7.02—7.23 (m, 4 Н, CHAr); 7.35, 8.03 (both m, 2 H each, CHAr);
9.99, 12.28, 12.42 (all s, 1 H each, NH)
4.85 (s)
4.90 (s)
–32.18 (m, 1 F);
4.75 (s, 3 F)
4.85 (s)
–29.76 (m, 1 F);
4.95 (s, 3 F)
–34.78, –29.73
(both m, 1 F each);
4.95 (s, 3 F)
10g
11a
7.42 (s, 3 H, Me); 4.07 (s, 3 H, MeO); 7.06 (t, 1 H, CHAr, J = 7.9); 7.26 (m, 5 H, CHAr);
7.52 (t, 1 H, CHAr, J = 7.9); 7.91 (d, 1 H, CHAr, J = 7.9); 9.99, 12.28, 12.42 (all s, 1 H each, NH)
1.03 (t, 3 H, Me, J = 7.8); 1.16 (s, 6 H, Me); 1.42, 1.59 (both m, 2 H each, CH2);
2.19 (АВ system, 2 H, CH2, J = 10.6); 2.64 (s, 2 H, CH2); 3.57 (m, 2 H, CH2N);
7.38 (m, 3 Н, CHAr); 7.84 (d, 2 H, CHAr, J = 7.8); 9.61 (s, 1 H, NH)
3.08 (s)
5.11 (s)
11b
11c
1.02, 1.08 (both s, 3 H each, Me); 2.15 (АВ system, 2 H, CH2, J = 10.6); 2.46 (s, 2 H, CH2);
4.88 (s, 2 H, CH2N); 7.36 (m, 8 Н, CHAr); 7.95 (d, 2 H, CHAr, J = 7.8); 9.73 (s, 1 H, NH)
0.96, 1.02 (both s, 3 H each, Me); 2.12 (s, 2 H, CH2); 2.16 (АВ system, 2 H, CH2, J = 17.4);
2.94, 3.84 (both m, 2 H each, CH2); 7.22—7.38 (m, 5 H, CHAr); 7.46 (m, 3 H, CHAr);
7.94 (d, 2 H, CHAr, J = 7.4); 9.62 (s, 1 H, NH)
5.08 (s)
5.17 (s)
11d
1.04, 1.11 (both s, 3 H each, Me); 2.22 (АВ system, 2 H, CH2, J = 15.2); 2.37, 2.42 (both s, 3 H each,
Me); 2.49 (m, 2 H, CH2); 7.17 (d, 2 H, CHAr, J = 8.0); 7.28, 7.41 (both d, 2 H each, CHAr, J = 8.1);
7.55 (d, 2 H, CHAr, J = 8.0); 7.28, 7.41 (both d, 2 H each, CHAr, J = 8.1) 9.46 (s, 1 H, NH)
5.19 (s)
11e
12a
1.07, 1.14 (both s, 3 H each, Me); 2.28 (АВ system, 2 H, CH2, J = 15.2); 2.47 (s, 3 H, Me); 2.53 (m, 2 H,
CH2); 6.56 (m, 1 H, HC=); 7.21—7.40 (m, 4 H, CHAr); 7.42, 7.72 (m, 1 H, CHAr); 9.46 (s, 1 H, NH)
1.05 (t, 3 Н, Ме, J = 7.5); 2.18 (s, 3 Н, Ме); 2.27 (q, 2 Н, СН2, J = 7.5);
9.17, 11.03 (both s, 1 H each, NH)
4.59 (s)
2.83 (s)
12b
12c
2.28 (s, 3 H, Me); 7.46, 7.97 (both d, 2 H each, CHAr, J = 8.4); 7.99, 11.22 (both s, 1 H each, NH)
2.28, 2.44 (both s, 3 H each, Ме); 7.19, 7.36 (both m, 2 H each, CHAr); 9.88,
11.21 (both s, 1 H each, NH)
3.64 (s)
3.20 (s)
13a
13b
13c
2.39 (s, 3 Н, Ме); 3.62 (s, 3 Н, МеO); 7.12, 7.99 (both m, 2 H each, CHAr);
9.25, 10.83 (both s, 1 H each, NH)
2.41 (s, 3 Н, Ме); 3.67 (s, 3 Н, МеO); 7.19 (m, 2 Н, CHAr); 7.47, 7.63 (both m, 1 H each, CHAr);
8.73 (d, 1 H NH, J = 7.2); 10.96 (s, 1 Н, NH)
2.42 (s, 3 Н, Ме); 3.68 (s, 3 Н, МеO); 4.93 (s, 2 Н, CH2); 7.17 (m, 2 Н, CHAr);
7.35 (m, 5 Н, CHAr); 8.06 (m, 2 Н, CHAr); 9.49 (s, 1 Н, NH)
–30.82 (m, 1 F);
1.26 (s, 3 F)
–34.21 (m, 1 F);
2.68 (s, 3 F)
–30.21 (m, 1 F);
4.68 (s, 3 F)
(to be continued)