New 2ꢀsubstituted 1,8ꢀnaphthyridines
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 9, September, 2007
1915
Table 4. IR spectroscopic data and 31P{1H} and 1H NMR spectroscopic data for naphthyridines 4b, 5b, and 9a,b
Comꢀ
pound
IR, ν/cm–1
ν(P=O)
NMR (CDCl3), δ (J/Hz)
ν
*
31P
1H
cycl
4b
1180
1620,
1600,
1560
33.1
1.89 (d, 3 H, Me, JH,P = 15.2); 2.15—2.24, 2.51—2.60, 2.85—2.91, 3.37—3.46
(all m, 1 H each, CH2); 7.02—7.07 (m, 2 H, mꢀHPh); 7.20—7.23 (m, 1 H, pꢀHPh);
7.35—7.42 (m, 3 H, 2 mꢀHPh + 1 H(6)); 7.51—7.54 (m, 3 H, 2 oꢀHPh + 1 pꢀHPh);
1
7.76 (s, 1 H, H(4)); 8.07 (dd, 1 H, H(5), JH,H = 1.9, 2JH,H = 8.0); 8.50—8.54
(m, 2 H, oꢀHPh); 9.06 (dd, 1 H, H(7), 1JH,H = 1.9, 2JH,H = 4.1)
5b
1169,
1182,
sh
1616,
1601,
1554
37.4
1.74—1.80 (m, 1 H, CH2); 1.84 (d, 3 H, Me, JH,P = 16.1); 1.98—2.10, 2.64—2.76
(both m, 2 H each, CH2); 2.85—2.91 (m, 1 H, CH2); 7.03—7.08 (m, 2 H, mꢀHPh);
7.20—7.24 (m, 1 H, pꢀHPh); 7.31—7.35 (m, 2 H, mꢀHPh); 7.44 (dd, 1 H, H(6),
1JH,H = 4.2, 2JH,H = 8.0); 7.52—7.54 (m, 3 H, 2 oꢀHPh + 1 pꢀHPh); 7.74 (s, 1 H,
H(4)); 8.07 (dd, 1 H, H(5), 1JH,H = 1.9, 2JH,H = 8.0); 8.40—8.45 (m, 2 H, oꢀHPh);
9.06 (dd, 1 H, H(7), 1JH,H = 1.9, 2JH,H = 4.2)
9а
9b
1183
1169
1610,
1549
32.6
38.2
3.01—3.08 (m, 2 H, CH2P); 3.34—3.41 (m, 2 H, CH2C); 7.35 (d, 1 H, H(3),
1JH,H = 8.2); 7.40—7.49 (m, 7 H, 4 mꢀHPh + 2 pꢀHPh + 1 H(6)); 7.77—7.82
(m, 4 H, oꢀHPh); 8.03 (d, 1 H, H(4), 1JH,H = 8.2); 8.13 (dd, 1 H, H(5),
1JH,H = 1.8, 2JH,H = 8.1); 9.06 (dd, 1 H, H(7), 1JH,H = 1.8, 2JH,H = 8.1)
1.32 (d, 6 H, Me, JH,P = 15.8); 3.35 (d, 2 H, CH2, JH,P = 7.8); 7.38 (d, 1 H, H(3),
JH,H = 8.4); 7.43 (dd, 1 H, H(6), 1JH,H = 8.2, 2JH,H = 4.2); 7.45—7.51 (m, 6 H,
mꢀHPh + pꢀHPh); 8.00—8.05 (m, 5 H, 4 oꢀHPh + 1 H(4)); 8.13 (dd, 1 H, H(5),
1JH,H = 8.2, 2JH,H = 2.0); 9.05 (dd, 1 H, H(7), 1JH,H = 4.2, 2JH,H = 2.0)
1607,
1553
* Skeletal vibrations of the naphthyridine rings.
Table 5. IR spectroscopic data and 31P{1H} and 1H NMR spectroscopic data for ketones 2b, 3b, and 6a,b—8a,b
Comꢀ
pound
IR, ν/cm–1
P=O C=O
NMR (CDCl3), δ (J/Hz)
31P
1H
2b
1175
1732
31.5
1.37 (d, 3 H, Me, JP,H = 15.8); 1.73—1.82 (m, 2 H, CH2); 1.89—1.97,
2.03—2.11, 2.23—2.30, 2.70—2.81 (all m, 1 H each, CH2); 7.40—7.44
(m, 2 H, pꢀHPh); 7.49—7.59 (m, 4 H, mꢀHPh); 7.78—7.86, 8.09—8.15
(both m, 2 H each, oꢀHPh
)
3b
1190
1710
36.2
1.31 (d, 3 H, Me, JP,H = 15.2); 1.59—1.78 (m, 4 H, 2 CH2); 2.20—2.28
(m, 2 H, CH2); 2.44—2.50, 2.82—2.90 (both m, 1 H each, CH2C(O));
7.38—7.43 (m, 2 H, pꢀHPh); 7.44—7.53 (m, 4 H, mꢀHPh); 7.76—7.80,
7.93—7.98 (both m, 2 H each, oꢀHPh
)
6а
6b
1190
1180
1700
1690
30.0
31.9
1.14—1.46, 1.84—2.07 (both m, 4 H each, 4 CH2); 2.30—2.34, 2.79—2.85
(both m, 1 H each, CH2C(O)); 3.53—3.60 (m, 1 H, CHP); 7.41—7.52
(m, 6 H, mꢀHPh + pꢀHPh); 7.72—7.79 (m, 4 H, oꢀHPh
)
1.11—1.28 (m, 2 H, CH2); 1.30—1.39 (m, 1 H, CH2); 1.34 (d, 3 H, Me,
JH,P = 16.0); 1.75—1.85 (m, 4 H, CH2); 2.22—2.27, 2.44—2.53, 2.66—2.72
(all m, 1 H each, CH2); 7.40—7.55 (m, 6 H, mꢀHPh + pꢀHPh); 7.76—7.81,
7.89—7.94 (both m, 2 H each, oꢀHPh
)
7а
7b
1180
1695
1690
30.1
32.2
1.08—1.19, 1.28—1.37, 1.41—1.50 (all m, 1 H each, CH2); 1.55—1.74
(m, 4 H, CH2); 1.80—1.87, 1.90—1.98, 2.04—2.09, 2.37—2.52, 2.82—2.89
(all m, 1 H each, CH2); 3.46—3.55 (m, 1 H, CHP); 7.40—7.55 (m, 6 H,
mꢀHPh + pꢀHPh); 7.72—7.80 (m, 4 H oꢀHPh
)
1180,
1190
0.74—0.84, 1.20—1.29 (both m, 1 H each, CH2); 1.30 (d, 3 H, Me, JH,P = 16.0);
1.44—1.81 (m, 6 H, CH2); 1.92—2.01, 2.94—3.09 (both m, 2 H each, CH2);
7.39—7.55 (m, 6 H, mꢀHPh + pꢀHPh); 7.78—7.87 (m, 4 H, oꢀHPh
)
8а
8b
1180
1720
1723
32.5
37.2
2.09 (s, 3 H, Me); 2.48—2.55 (m, 2 H, CH2C(O)); 2.71—2.77 (m, 2 H,
CH2P); 7.42—7.53 (m, 6 H, mꢀHPh + pꢀHPh); 7.67—7.74 (m, 4 H oꢀHPh
1.39 (d, 6 H, CMe2, JH,P = 16.2); 2.08 (s, 3 H, C(O)Me); 2.70 (d, 2 H, CH2,
JH,P = 7.7); 7.45—7.53 (m, 6 H, mꢀHPh + pꢀHPh); 7.93—7.98 (m, 4 H, oꢀHPh
)
1173,
1185 sh
)