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New Journal of Chemistry
Page 7 of 10
DOI: 10.1039/C8NJ02127A
Journal Name
ARTICLE
IR (KBr): νmax 2985, 1789, 1721, 1656, 1475, 1325, 1178, 1085, 996, 7.0, 1.5 Hz, 4H), 7.39 (dt, J = 4.1, 1.8 Hz, 1H), 6.04 (dd, J = 6.3, 4.1
789, 645 cm-1;1H NMR (400 MHz, CDCl3) δ 8.04 – 8.00 (m, 2H), 7.90 Hz, 1H), 3.53 (td, J = 9.7, 6.1 Hz, 1H), 3.02 (dd, J = 6.6, 3.4 Hz, 1H),
(dd, J = 3.9, 2.1 Hz, 2H), 7.84 – 7.81 (m, 2H), 7.64 (dd, J = 8.5, 5.3 Hz, 2.17 – 2.01 (m, 2H), 1.97 – 1.83 (m, 2H). 13C NMR (100 MHz, CDCl3)
2H), 4.92 (dd, J = 15.6, 12.5 Hz, 2H), 4.37 – 4.28 (m, 1H), 3.82 (d, J = δ 196.5, 193.9, 193.1, 143.5, 142.3, 137.3, 136.3, 131.7, 129.6,
8.7 Hz, 1H), 3.76 (t, J = 8.4 Hz, 1H), 2.98 – 2.90 (m, 1H), 2.70 (td, J = 128.4, 127.3, 126.0, 124.4, 124.3, 119.9, 90.1, 49.3, 30.0, 24.6. MS
9.5, 3.6 Hz, 1H), 2.31 – 2.23 (m, 2H), 2.06 – 1.99 (m, 1H), 1.90 – 1.83 (ESI) m/z = 349 [M+H]+
(m, 1H). 13C NMR (100 MHz, CDCl3) δ 199.0, 197.3, 189.3, 175.6,
174.8, 170.4, 141.9, 140.0, 136.7, 136.5, 135.1, 133.1, 132.4, 132.2,
1'-(3-chlorophenylimino)-5',6',7',7a'-tetrahydro-1'H-spiro[indene-
2,3'-pyrrolo[1,2-c]thiazole]-1,3-dione (8b): Yellow solid; Mp 121-
131.7, 131.5, 129.6, 129.3, 124.2, 123.7, 72.6, 67.9, 54.0, 48.1, 47.2,
123°C; IR (KBr): νmax 3020, 1747, 1714, 1591, 1448, 1243, 1215,
44.9, 25.9, 24.7. MS (ESI) m/z = 507 [M+H]+; HRMS (ESI) Calcd.
1045, 752, 668 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.13 – 8.12 (m,
C25H19O5N2Br [M+H]+: 507.05766, found: 507.05501.
1H), 8.07 (dd, J = 4.0, 2.5 Hz, 1H), 7.94 – 7.90 (m, 2H), 7.49 (t, J = 1.9
3-chloro-6',7',8',8a'-tetrahydro-1'H,12H-spiro[indolo[2,1-
b]quinazoline-6,4'-pyrrolo[3,4-a]pyrrolizine]-
Hz, 1H), 7.45 – 7.41 (m, 1H), 7.38 – 7.35 (m, 2H), 6.04 (dd, J = 6.4,
3.7 Hz, 1H), 3.53 (td, J = 9.7, 6.3 Hz, 1H), 3.05 – 2.99 (m, 1H), 2.21 –
1',3',12(2'H,3a'H,8b'H)-trione (9a): Yellow solid; Mp 251-253°C; IR 2.13 (m, 1H), 2.07 – 2.03 (m, 1H), 1.93 – 1.85 (m, 2H). 13C NMR (100
(KBr): νmax 3086, 2958, 1773, 1716, 1675, 1606, 1477, 1328, 1194, MHz, CDCl3) δ 196.2, 194.5, 193.2, 143.5, 142.2, 138.4, 136.4, 135.1,
833, 769 cm-1; 1H NMR (300 MHz, CDCl3+DMSO-d6) δ 8.52 (d, J = 8.6 131.7, 130.5, 128.5, 127.5, 126.1, 124.4, 124.1, 119.9, 90.0, 49.2,
Hz, 1H), 8.36 (d, J = 7.2 Hz, 1H), 7.80 (dd, J = 13.3, 10.1, Hz, 2H), 7.58 29.9, 24.5. MS (ESI) m/z = 383 [M+H]+
(d, J = 1.3 Hz, 1H), 7.46 (dd, J = 8.6, 2.1 Hz, 1H), 7.28 (d, J = 2.0 Hz,
1H), 4.59 (q, J = 7.1 Hz, 1H), 3.94 (d, J = 7.7 Hz, 1H), 3.60 (t, J = 7.5
1'-(4-chlorophenylimino)-5',6',7',7a'-tetrahydro-1'H-spiro[indene-
2,3'-pyrrolo[1,2-c]thiazole]-1,3-dione (8c): Yellow solid; Mp 124-
126°C; IR (KBr): νmax 3024, 1749, 1725, 1652, 1489, 1285, 1089, 756,
Hz, 1H), 2.62 – 2.57 (m, 1H), 2.43 (t, J = 6.9 Hz, 1H), 2.19 – 2.06 (m,
2H), 2.05 – 1.93 (m, 2H). 13C NMR (75 MHz, CDCl3+DMSO-d6) δ
669 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.13 – 8.05 (m, 2H), 7.93 –
182.3, 180.9, 164.1, 163.7, 151.4, 143.2, 139.4, 136.0, 135.0, 134.5,
7.90 (m, 2H), 7.48 – 7.39 (m, 4H), 6.02 (dd, J = 6.4, 3.8 Hz, 1H), 3.51
132.9, 132.3, 131.4, 131.3, 126.2, 122.4, 72.9, 69.5, 65.5, 50.3, 46.4,
(td, J = 9.6, 6.3 Hz, 1H), 3.04 – 2.98 (m, 1H), 2.19 – 2.13 (m, 1H),
31.2, 27.7. MS (ESI) m/z = 433 [M+H]+; HRMS (ESI) Calcd. C23H17O3N4
2.06 – 2.05 (m, 1H), 1.93 – 1.85 (m, 2H). 13C NMR (100 MHz, CDCl3)
[M+H]+: 433.10819, found: 433.10619.
δ 196.3, 194.4, 193.3, 183.7, 143.5, 142.3, 136.4, 134.1, 131.7,
3-fluoro-6',7',8',8a'-tetrahydro-1'H,12H-spiro[indolo[2,1-
b]quinazoline-6,4'-pyrrolo[3,4-a]pyrrolizine]-
129.8, 129.8, 127.2, 126.9, 124.4, 124.3, 119.9, 89.9, 49.2, 30.0,
24.5. MS (ESI) m/z = 383 [M+H]+
1',3',12(2'H,3a'H,8b'H)-trione (9b):Brown solid; Mp 257-259°C; IR
(KBr): νmax 3199, 2989, 1789, 1721, 1657, 1606, 1478, 1389, 1256,
1085, 833, 769 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.55 – 8.50 (m,
1H), 8.32 (d, J = 8.0 Hz, 1H), 7.88 – 7.79 (m, 1H), 7.75 (d, J = 8.1 Hz,
1H), 7.56 (t, J = 7.5 Hz, 1H), 7.23 (t, J = 2.5 Hz, 1H), 7.01 (d, J = 3.5
Hz, 1H), 4.58 (q, J = 7.3 Hz, 1H), 3.96 (d, J = 7.6 Hz, 1H), 3.59 (td, J =
7.5, 2.2 Hz, 1H), 2.57 (d, J = 1.8 Hz, 2H), 2.43 – 2.37 (m, 1H), 2.15 –
2.05 (m, 1H), 1.93 (dd, J = 19.9, 3.9 Hz, 2H). 13C NMR (75 MHz,
CDCl3+DMSO-d6) δ 182.1, 180.3, 166.8, 164.1, 163.8, 151.3, 140.5,
139.3, 132.8, 132.2, 131.3, 126.3, 122.6, 122.5, 121.6, 121.5, 118.8,
118.5, 73.0, 69.5, 65.6, 50.4, 46.4, 31.2, 27.8. MS (ESI) m/z = 417
[M+H]+; HRMS (ESI) Calcd. C23H18O3N4F [M+H]+: 417.13439, found:
417.13575.
1'-(4-fluorophenylimino)-5',6',7',7a'-tetrahydro-1'H-spiro[indene-
2,3'-pyrrolo[1,2-c]thiazole]-1,3-dione (8d): Yellow solid; Mp 118-
120°C; IR (KBr): νmax 3020, 1749, 1712, 1509, 1407, 1276, 1214,
1046, 747, 667 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.14 – 8.05 (m,
2H), 7.94 – 7.89 (m, 2H), 7.43 (dd, J = 4.4, 2.4 Hz, 2H), 7.21 (t, J = 2.7
Hz, 2H), 5.98 (dd, J = 6.2, 4.0 Hz, 1H), 3.52 (td, J = 9.7, 6.3 Hz, 1H),
3.05 – 3.00 (m, 1H), 2.17 – 2.03 (m, 2H), 1.94 – 1.83 (m, 2H). 13
C
NMR (100 MHz, CDCl3) δ 196.4, 194.5, 193.3, 143.5, 142.3, 136.4,
133.2, 131.7, 128.0, 127.9, 127.4, 124.4, 124.3, 120.0, 116.8, 116.6,
90.16, 49.2, 30.0, 24.5. MS (ESI) m/z = 367 [M+H]+
1'-(4-methoxyphenylimino)-5',6',7',7a'-tetrahydro-1'H-
spiro[indene-2,3'-pyrrolo[1,2-c]thiazole]-1,3-dione (8e): Yellow
solid; Mp 125-127°C; IR (KBr): νmax 3020, 2985, 1714, 1705, 1511,
1479, 1345, 1214, 1046, 931, 742, 667 cm-1; 1H NMR (400 MHz,
CDCl3) δ 8.13 – 8.05 (m, 2H), 7.94 – 7.88 (m, 2H), 7.35 (s, J = 2.1 Hz,
1H), 7.01 (d, J = 2.1 Hz, 1H), 5.94 (dd, J = 6.2, 4.2 Hz, 1H), 3.83 (s,
3H), 3.51 (dt, J = 9.6, 4.8 Hz, 1H), 3.03 – 2.98 (m, 1H), 2.15 – 2.02
(m, 2H), 1.99 – 1.83 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 196.6,
193.9, 193.5, 159.3, 143.5, 142.3, 136.3, 136.3, 129.8, 127.3, 124.4,
124.3, 114.9, 114.8, 90.2, 84.9, 55.5, 55.4, 49.2, 30.0, 24.6. MS (ESI)
m/z = 379 [M+H]+
7-benzyl-3'-fluoro-7-methyl-2,3,8a,8b-tetrahydro-1H,12'H-
spiro[cyclopenta[a]pyrrolizine-5,6'-indolo[2,1-b]quinazoline]-
6,8,12'(5aH,7H)-trione (9c): Brown solid; Mp 220-222°C; IR (KBr):
ν
max 2906, 1784, 1723, 1568, 1324, 1275, 1178, 1040, 986, 976, 888,
756, 668 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.59 (dd, J = 8.9, 4.8 Hz,
1H), 8.33 (d, J = 8.0 Hz, 1H), 7.70 (t, J = 1.2 Hz, 1H), 7.52 – 7.45 (m,
2H), 7.33 – 7.30 (m, 3H), 7.22 (dd, J = 8.8, 2.6 Hz, 1H), 7.16 (dd, J =
8.0, 2.5 Hz, 1H), 7.05 – 7.01 (m, 2H), 4.69 (dd, J = 9.4, 5.9 Hz, 1H),
3.54 (d, J = 12.4 Hz, 1H), 2.88 (s, 2H), 2.78 (dd, J = 12.4, 5.9 Hz, 1H),
2.67 – 2.58 (m, 2H), 2.38 – 2.34 (m, 1H), 1.93 – 1.78 (m, 3H), 1.15 (s,
3H). 13C NMR (100 MHz, CDCl3) δ 216.1, 215.9, 162.0, 159.7, 159.1,
146.3, 136.6, 135.0, 134.5, 130.6, 129.7, 128.7, 127.8, 127.4, 126.9,
121.8, 118.8, 118.8, 117.5, 117.2, 113.1, 112.8, 76.1, 66.9, 64.7,
60.8, 60.5, 50.0, 46.0, 31.0, 25.4, 18.0. MS (ESI) m/z = 520 [M+H]+;
HRMS (ESI) Calcd. C32H27O3N3F [M+H]+: 520.20145, found:
520.20310.
1'-(4-(trifluoromethyl)phenylimino)-5',6',7',7a'-tetrahydro-1'H-
spiro[indene-2,3'-pyrrolo[1,2-c]thiazole]-1,3-dione (8f): Pale yellow
solid; Mp 132-134°C; IR (KBr): νmax 3156, 2989, 1789, 1721, 1653,
1528, 1384, 1287, 1089, 986, 758, 667 cm-1; 1H NMR (500 MHz,
CDCl3) δ 8.13 (d, J = 5.5 Hz, 1H), 8.07 (d, J = 5.3 Hz, 1H), 7.93 (t, J =
9.0 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 7.65 (d, J = 8.3 Hz, 2H),6.14 (dd,
6.4,3.5 Hz), 3.53 (dt, J = 16.0, 8.1 Hz, 1H), 3.05 – 3.00 (m, 1H), 2.30 –
2.18 (m, 1H), 2.07 – 2.03 (m, 1H), 1.90 – 1.85 (m, 2H). 13C NMR (100
MHz, CDCl3) δ 196.1, 194.7, 193.1, 183.7, 150.2, 143.6, 142.2, 136.4,
131.7, 126.6, 125.9, 124.5, 124.4, 120.0, 89.9, 58.5, 49.3, 32.8, 30.0,
24.5, 19.0. MS (ESI) m/z = 417 [M+H]+
1'-(phenylimino)-5',6',7',7a'-tetrahydro-1'H-spiro[indene-2,3'-
pyrrolo[1,2-c]thiazole]-1,3-dione (8a): Yellow solid; Mp 131-133°C;
IR (KBr): νmax 2985, 1747, 1712, 1593, 1462, 1311, 1275, 1214, 1044,
743, 666 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.13 – 8.09 (m, 1H), 8.06
(ddd, J = 5.6, 2.7, 1.7 Hz, 1H), 7.92 – 7.89 (m, 2H), 7.47 (tdd, J = 8.4,
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