BIODYNAMIC SPIROHETEROCYCLES
2915
1
nmax (KBr): 3401, 3284, 3218, 2935, 1698, 1658, 1610, 1226 cmꢂ1. H NMR
(DMSO-d6, 300 MHz): d 0.82 (t, J ¼ 7.2 Hz, 3H, CH3), 0.98 (s, 3H, CH3), 1.01 (s,
3H, CH3), 2.07 (d, J ¼ 16.4 Hz, 1H, CH), 2.2 (d, J ¼ 16.4 Hz, 1H, CH), 2.56 (d,
J ¼ 6.2 Hz, 2H, CH2), 3.67 (q, J ¼ 7.4 Hz, 2H, CH2), 6.68 (d, J ¼ 7.4 Hz, 1H), 6.76
(s, 1H), 6.85 (d, J ¼ 7.2 Hz, 1H), 7.74 (br s, 2H, NH2, D2O exchangeable), 10.19
(s, 1H, NH, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz): d 13.6, 27.2,
28.5, 32.3, 47.2, 51.4, 59.2, 76.8, 108.6, 113.7, 116.9, 121.9, 128.4, 136.9, 145.8,
159.2, 160.4, 162.8, 168.7, 180.6, 195.3. MS (m=z): 416 (Mþ). Anal. calcd. for
C21H21Cl N2O5: C, 60.51; H, 5.08; N, 6.72. Found: C, 60.72; H, 5.01; N, 6.55.
Compound 7d. Ethyl 2-amino-50-bromo-7,7-dimethyl-20,5-dioxo-5,6,7,8-
tetrahydrospiro [chromene-4,30 indoline]-3-carboxylate. White crystalline solid
(yield: 92%); mp: 296–298 ꢀC.
1
nmax (KBr): 3398, 3282, 3209, 2934, 1700, 1662, 1612, 1223 cmꢂ1. H NMR
(DMSO-d6, 300 MHz): d 0.82 (t, J ¼ 7.2 Hz, 3H, CH3), 0.99 (s, 3H, CH3), 1.01 (s,
3H, CH3), 2.06 (d, J ¼ 16.4 Hz, 1H, CH), 2.2 (d, J ¼ 16.4 Hz, 1H, CH), 2.54 (d,
J ¼ 6.2 Hz, 2H, CH2), 3.68 (q, J ¼ 7.2 Hz, 2H, CH2), 6.67 (d, J ¼ 7.2 Hz, 1H), 6.76
(s, 1H), 6.86 (d, J ¼ 7.4 Hz, 1H), 7.72 (br s, 2H, NH2, D2O exchangeable), 10.20
(s, 1H, NH, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz): d 13.3, 27.4,
28.5, 32.6, 47.2, 51.5, 59.2, 76.3, 108.6, 111.7, 118.9, 121.9, 128.5, 136.9, 145.8,
159.7, 161.4, 161.9, 168.7, 181.1, 195.6. MS (m=z): 461 (Mþ). Anal. calcd. for
C21H21Br N2O5: C, 54.68; H, 4.59; N, 6.07. Found: C, 54.85; H, 4.48; N, 5.92.
Compound
7e. Ethyl
2-amino-7,7-dimethyl-50-nitro-20,5-dioxo-5,6,7,8-
tetrahydrospiro [chromene-4,30 indoline]-3-carboxylate. White crystalline solid
(yield: 92%); mp: 276–278 ꢀC.
nmax (KBr): 3406, 3288, 3212, 2935, 1702, 1662, 1618, 1225 cmꢂ1. H NMR
1
(DMSO-d6, 300 MHz): d 0.83 (t, J ¼ 7.4 Hz, 3H, CH3), 0.99 (s, 3H, CH3), 1.02 (s,
3H, CH3), 2.07 (d, J ¼ 16.2 Hz, 1H, CH), 2.2 (d, J ¼ 16.2 Hz, 1H, CH), 2.58 (d,
J ¼ 6.8 Hz, 2H, CH2), 3.71 (q, J ¼ 7.6, 2H, CH2), 6.86 (d, J ¼ 7.6 Hz, 1H), 6.98 (s,
1H), 7.27 (d, J ¼ 7.6 Hz, 1H), 7.78 (br s, 2H, NH2, D2O exchangeable), 11.39 (s,
1H, NH, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz): d 13.5, 27.8, 28.6,
32.4, 47.6, 51.9, 59.2, 76.3, 108.6, 112.8, 121.9, 123.9, 132.5, 138.9, 148.8, 159.9,
163.4, 164.1, 168.7, 181.4, 195.7. MS (m=z): 427 (Mþ). Anal. calcd. for C21H21
N3O7: C, 59.01; H, 4.95; N, 9.83. Found: C, 58.85; H, 4.82; N, 9.92.
Compound
7f. Ethyl
2-amino-50,70,7,7-tetramethyl-20,5-dioxo-5,6,7,8-
tetrahydrospiro[chromene-4,30-indoline]-3-carboxylate. White crystalline solid
(yield: 95%); mp: 280–282 ꢀC.
nmax (KBr): 3398, 3282, 3210, 2934, 1698, 1652, 1615, 1223 cmꢂ1. H NMR
1
(DMSO-d6, 300 MHz): d 0.82 (t, J ¼ 7.2 Hz, 3H, CH3), 0.99 (s, 3H, CH3), 1.02 (s,
3H, CH3), 2.03 (d, J ¼ 16.2 Hz, 1H, CH), 2.18 (d, J ¼ 16.2 Hz, 1H, CH), 2.24 (s,
3H, CH3), 2.32 (s, 3H, CH3), 2.57 (d, J ¼ 6.2 Hz, 2H, CH2), 3.69 (q, J ¼ 7.4 Hz,
2H, CH2), 6.64 (s, 1H), 6.72 (s, 1H), 7.74 (br s, 2H, NH2, D2O exchangeable),
10.20 (s, 1H, NH, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz): d 13.4,
21.2, 22.7, 27.2, 28.5, 32.4, 47.5, 51.5, 59.2, 76.6, 108.6, 113.7, 121.4, 122.7, 127.3,
136.9, 144.8, 159.7, 160.8, 162.8, 168.6, 180.7, 195.4. MS (m=z): 410 (Mþ). Anal.
calcd. for C23H26N2O5: C, 67.30; H, 6.38; N, 6.82. Found: C, 67.52; H, 6.31; N, 7.07.