J
S. Belveren et al.
Paper
Synthesis
1H NMR (400 MHz, DMSO-d6): δ = 2.59 (s, 3 H, NCH3), 3.12 (dd, J =
6.18, 5.14 Hz, 1 H), 3.22 (d, J = 14.24 Hz, 1 H), 3.42 (d, J = 14.20 Hz, 1
H), 3.50 (d, J = 4.96 Hz, 1 H), 3.54 (s, 3 H, OCH3), 4.06 (d, J = 5.36 Hz, 1
H, NH), 4.66 (dd, J = 5.90, 5.90 Hz, 1 H), 7.40–7.02 (m, 9 H, ArH), 7.70
(d, J = 7.76 Hz, 1 H, ArH), 11.00 (br s, 1 H, NH).
13C NMR (100 MHz, DMSO-d6): δ = 24.4, 28.8, 51.1, 52.1, 54.1, 65.3,
70.9, 107.6, 111.5, 118.2, 118.6, 121.0, 121.0, 124.7, 125.2, 126.2,
127.3, 127.4, 125.2, 126.2, 127.3, 127.4, 130.0,132.9, 135.9, 143.9,
171.5 (C=O), 176.1 (C=O), 178.9 (C=O).
IR (ATR): 3315, 3060, 2983, 2950, 1782, 1739, 1703, 1595, 1436, 1392,
1253, 1240, 1164, 981, 747 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 3.30 (d, J = 14.18 Hz, 1 H), 3.43 (dd,
J = 5.42, 4.48 Hz, 1 H), 3.55 (d, J = 14.12 Hz, 1 H), 3.58 (s, 3 H, OCH3),
3.72 (d, J = 4.44 Hz, 1 H), 4.24 (d, J = 5.48 Hz, 1 H, NH), 4.78 (dd, J =
5.42, 5.42 Hz, 1 H), 7.53–6.64 (m, 13 H, ArH), 7.75 (d, J = 7.80 Hz, 1 H,
ArH), 11.08 (br s, 1 H, NH).
13C NMR (100 MHz, DMSO-d6): δ = 30.5, 52.5, 52.8, 55.9, 66.6, 72.7,
109.3, 112.4, 119.6, 120.0, 122.5, 125.8, 126.0, 127.4, 127.5 (2 C),
128.4, 128.7, 129.1, 129.4 (2 C), 131.0, 133.3, 134.8, 137.5, 145.3,
173.1 (C=O), 176.3 (C=O), 179.1 (C=O).
MS (ESI, M + H+): m/z = 417.4 (M + H+, 100%).
HRMS (DIP): m/z [M+] calcd for C24H23N3O4: 417.1694; found:
417.1688.
MS (ESI, M – H+): m/z (%) = 512.2 (M – H+, 100), 514.2 (M + H+, 35).
HRMS (DIP): m/z [M+] calcd for C29H24ClN3O4: 513.1455; found:
513.1450.
Methyl (2S,3S,6aR)-6a-[(1H-Indol-3-yl)methyl)-4,6-dioxo-5-phe-
nyl-2-(pyridin-2-yl)octahydropyrrolo[3,4-b]pyrrole-3-carboxyl-
ate (5gc)
Methyl (2S,3S,6aR)-6a-[(1H-Indol-3-yl)methyl]-2-(3-chlorophe-
nyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-b]pyrrole-3-car-
boxylate (5gf)
After 36 h and workup, the product was crystallized as colorless
prisms; yield: 441 mg (92%); mp 219–221 °C (dec.).
IR (ATR): 3352, 3058, 2981, 1712, 1595, 1541, 1436, 1383, 1099, 744
After 26 h and workup, the product was crystallized as colorless
prisms; yield: 429 mg (95%); mp 152–154 °C.
cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 3.39–3.30 (m, 2 H), 3.43 (s, 3 H,
OCH3), 3.67–3.60 (m, 2 H), 4.45 (dd, J = 8.24, 8.20 Hz, 1 H), 7.80–6.94
(m, 13 H, ArH), 8.72 (br d, J = 4.16 Hz, 1 H, ArH), 10.91 (br s, 1 H, NH).
13C NMR (100 MHz, DMSO-d6): δ = 20.2, 51.1, 52.3, 66.9, 72.5, 107.5,
111.6, 118.3, 118.7, 121.1, 121.3, 122.5, 124.7, 126.1 (2 C), 127.4,
128.2, 128.6 (2 C), 131.6, 136.0, 136.9, 148.6, 160.2, 172.7 (C=O),
175.1 (C=O), 178.8 (C=O).
IR (ATR): 3344, 3270, 3060, 2982, 2949, 1780, 1737, 1705, 1378, 1288,
1173, 747, 681 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 2.59 (s, 3 H, NCH3), 3.13 (dd, J =
6.36, 4.96 Hz, 1 H), 3.22 (d, J = 14.20 Hz, 1 H)), 3.43 (d, J = 14.20 Hz, 1
H), 3.50 (d, J = 4.88 Hz, 1 H), 3.54 (s, 3 H, OCH3), 4.06 (d, J = 5.28 Hz, 1
H, NH), 4.66 (dd, J = 5.68, 5.68 Hz, 1 H), 7.40–7.02 (m, 8 H, ArH), 7.70
(d, J = 7.76 Hz, 1 H, ArH), 11.00 (br s, 1 H, NH).
MS (ESI, M + H+): m/z = 481.2 (M + H+, 100%).
HRMS (DIP): m/z [M+] calcd for C28H24N4O4: 480.1798; found:
13C NMR (100 MHz, DMSO-d6): δ = 24.1, 28.8, 51.1, 52.1, 54.1, 65.3,
70.9, 107.6, 111.5, 118.2, 118.6, 121.0, 124.7, 125.2, 126.2, 127.3,
127.4, 130.0, 132.9, 135.9, 143.9, 171.5 (C=O), 176.1 (C=O), 178.8
(C=O).
480.1704.
MS (ESI, M + H+): m/z (%) = 452.2 (M + H+, 100), 454.2 (M + H+, 35).
HRMS (DIP): m/z [M+] calcd for C24H22ClN3O4: 451.1299; found:
Methyl (2S,3S,6aR)-6a-[(1H-Indol-3-yl)methyl]-5-methyl-4,6-di-
oxo-2-(pyridin-2-yl)octahydropyrrolo[3,4-b]pyrrole-3-carboxyl-
ate (5gd)
451.1301.
After 36 h and workup, the product was crystallized as colorless
prisms; yield: 355 mg (85%); mp 198–200 °C (dec.).
Methyl (2S,3S,3aS,6aR)-6a-[(1H-Indol-3-yl)methyl]-1-(benzoylcar-
bamothioyl)-4,6-dioxo-2,5-diphenyloctahydropyrrolo[3,4-b]pyr-
role-3-carboxylate (6ga)
IR (ATR): 3355, 2981, 2972, 2889, 1975, 1774, 1698, 1520, 1432, 1380,
1251, 1150, 1073, 955, 775, 741 cm–1
.
After 24 h and workup, the product was crystallized as pale yellow
prisms; 552 mg (86%); mp 150–152 °C.
1H NMR (400 MHz, DMSO-d6): δ = 2.33 (s, 3 H, NCH3), 3.15 (d, J =
14.08 Hz, 1 H), 3.39 (d, J = 14.08 Hz, 1 H), 3.47 (d, J = 2.64 Hz, 1 H),
3.57 (s, 3 H, OCH3), 3.79 (dd, J = 3.01, 2.76 Hz, 1 H), 4.07 (d, J = 5.36 Hz,
1 H, NH), 4.78 (dd, J = 4.74, 3.34 Hz, 1 H), 7.47–6.99 (m, 6 H, ArH),
7.75–7.67 (m, 2 H, ArH), 8.40–8.38 (m, 1 H, ArH), 10.97 (br s, 1 H, NH).
13C NMR (100 MHz, DMSO-d6): δ = 159.9, 148.5, 136.6, 135.8, 127.4,
124.6, 122.3, 121.0, 120.9, 118.6, 118.1, 111.5, 107.6, 72.1, 66.7, 52.2,
51.7, 50.8, 29.5, 24.1, 29.5, 50.8, 51.7, 52.2, 66.7, 72.1, 107.6, 111.5,
118.1, 118.6, 120.9, 121.0, 122.3, 124.6, 127.4, 135.8, 136.6, 148.5,
159.9, 172.5 (C=O), 176.1 (C=O), 179.5 (C=O).
IR (ATR): 3202, 3060, 2981, 2889, 1787, 1739, 1702, 1537, 1492, 1389,
1252, 1202, 923, 743, 704 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 2.78 (s, 3 H, OCH3), 3.46 (dd, J =
1.76, 1.76 Hz, 1 H), 3.91 (br s, 2 H), 4.22 (d, J = 1.44 Hz, 1 H), 6.80 (br s,
1 H), 7.72–7.00 (m, 17 H, ArH), 8.11 (d, J = 7.40 Hz, 2 H, ArH), 11.33 (br
s, 1 H, NH), 11.60 (br s, 1 H, NH).
13C NMR (100 MHz, DMSO-d6): δ = 26.7, 50.1, 51.5, 54.2, 69.2, 74.2,
104.5, 111.4, 118.1, 118.8, 121.1, 125.1 (2 C), 126.2, 126.5 (2 C), 127.3,
127.8, 127.8 (2 C), 128.8 (2 C), 129.0 (2 C), 129.6 (2 C), 129.2, 130.8,
133.0, 133.3, 135.4, 138.5, 165.1 (C=O), 168.7 (C=O), 173.9 (C=O),
176.4 (C=O), 179.7 (C=S).
MS (ESI, M + H+): m/z = 419.2 (M + H+, 100%).
HRMS (DIP): m/z [M+] calcd for C23H22N4O4: 418.1641; found:
418.1649.
MS (ESI, M + H+): m/z = 643.2 (M + H+, 100%).
HRMS (DIP): m/z [M+] calcd for C37H30N4O5S: 642.1937; found:
642.1930.
Methyl (2S,3S,6aR)-6a-[(1H-Indol-3-yl)methyl]-2-(3-chlorophe-
nyl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-b]pyrrole-3-carbox-
ylate (5ge)
After 36 h and workup, the product was crystallized as colorless
prisms; yield: 503 mg (98%); mp 169–171 °C.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–M