816
Chem. Pharm. Bull.
Vol. 66, No. 8 (2018)
Found 713.2810.
1221 and 828cm−1; ESI-HR-MS Calcd for C40H38N6NaO4
(S,Z)-11-((E)-2-oxo-4-(quinolin-3-yl)but-3-en-1-ylidene)- 689.2852 [2M+Na]+; Found 689.2851.
1,2,3,10,11,11a-hexahydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-
5-one (10g)
(S,Z)-11-((E)-4-(5-Iodofuran-2-yl)-2-oxobut-3-en-1-ylidene)-
1,2,3,10,11,11a-hexahydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-
The compound was synthesized according to the general 5-one (10j)
procedure in 6% yield after ODS purification as a yellow pig-
The compound was synthesized according to the general
ment.
procedure in 1% yield after ODS purification as a yellow pig-
Spectral Data of 10g
ment.
1
[α]D20 +269 (c 0.1, MeOH); H-NMR (400MHz, acetone-d6)
Spectral Data of 10j
δ: 13.40 (s, 1H), 9.23 (d, J=2.2Hz, 1H), 8.53 (d, J=2.2Hz,
[α]D20 +361 (c 0.1, MeOH); 1H-NMR (400MHz, acetone-
1H), 8.05 (d, J=8.4Hz, 1H), 7.99 (d, J=7.8Hz, 1H), 7.91 d6) δ: 13.34 (brs, 1H), 7.90 (dd, J=8.0, 1.6Hz, 1H), 7.54 (td,
(dd, J=8.0, 1.6Hz, 1H), 7.81 (d, J=16Hz, 1H), 7.78 (ddd, J=8.0, 1.6Hz, 1H), 7.32 (d, J=16Hz, 1H), 7.25 (td, J=8.0,
J=8.0, 7.2, 1.6Hz, 1H), 7.63 (ddd, J=8.4, 7.2, 1.2Hz, 1H), 1.2Hz, 1H), 7.15 (d, J=8.0Hz, 1H), 6.81 (d, J=3.4Hz, 1H),
7.56 (ddd, J=7.8, 7.2, 1.2Hz, 1H), 7.34 (d, J=16Hz, 1H), 7.27 6.76 (d, J=16Hz, 1H), 6.73 (d, J=3.4Hz, 1H), 5.81 (s, 1H),
(td, J=8.0, 1.2Hz, 1H), 7.20 (d, J=7.2Hz, 1H), 5.86 (s, 1H), 4.45 (d, J=6.8Hz, 1H), 3.70–3.67 (m, 1H), 3.60–3.53 (m, 1H),
4.48 (d, J=7.6Hz, 1H), 3.74–3.68 (m, 1H), 3.62–3.55 (m, 1H), 2.64–2.59 (m, 1H), 2.30–2.19 (m, 1H), 2.14–2.06 (m, 2H);
2.60–2.55 (m, 1H), 2.34–2.26 (m, 1H), 2.15–2.06 (m, 2H); 13C-NMR (150MHz, acetone-d6) δ: 188.5, 165.6, 162.0, 158.2,
13C-NMR (150MHz, acetone-d6) δ: 188.8, 165.6, 162.3, 150.5, 138.0, 133.2, 131.9, 128.6, 127.2, 125.4, 125.0, 124.2, 122.9,
149.3, 136.7, 135.8, 133.2, 131.9, 130.9, 130.8, 130.1, 130.0, 117.6, 93.5, 93.4, 56.1, 47.5, 27.6, 24.2; IR (ATR); 3019, 1740,
129.6, 129.3, 128.8, 128.7, 128.1, 125.1, 123.0, 93.3, 56.1, 47.5, 1547, 1512, 1459, 1366, 1222 and 864cm−1; ESI-HR-MS Calcd
27.6, 24.2; IR (ATR); 3202, 2977, 1741, 1646, 1516, 1367, 1217, for C40H34I2N4NaO6 943.0465 [2M+Na]+; Found 943.0503.
705 and 637cm−1; ESI-HR-MS Calcd for C25H22N3O2 396.1712
(S, Z )-11-((E )- 4-(5-Bromofuran-2-yl)-2-oxobut-3-
en-1-ylidene)-1,2,3,10,11,11a-hexahydro-5H-benzo[e]pyrrolo-
[M+H]+; Found 396.1748.
(S,Z)-11-((E)-4-(Benzo[d][1,3]dioxol-5-yl)-2-oxobut-3- [1,2-a][1,4]diazepin-5-one (10k)
en-1-ylidene)-1,2,3,10,11,11a-hexahydro-5H-benzo[e]pyrrolo-
[1,2-a][1,4]diazepin-5-one (10h)
The compound was synthesized according to the general
procedure in 3% yield after ODS purification as a yellow pig-
The compound was synthesized according to the general ment.
procedure in 13% yield as a yellow pigment.
Spectral Data of 10h
Spectral Data of 10k
[α]D20 +196 (c 0.1, MeOH); 1H-NMR (600MHz, acetone-
[α]D20 +366 (c 1.0, MeOH); 1H-NMR (400MHz, acetone- d6) δ: 13.33 (brs, 1H), 7.90 (dd, J=8.4, 1.6Hz, 1H), 7.54 (td,
d6) δ: 13.34 (brs, 1H), 7.89 (dd, J=7.6, 1.6Hz, 1H), 7.54 (d, J=8.4, 1.6Hz, 1H), 7.31 (d, J=16Hz, 1H), 7.25 (td, J=8.4,
J=16Hz, 1H), 7.53 (ddd, J=8.4, 7.6, 1.6Hz, 1H), 7.24 (td, 1.8Hz, 1H), 7.16 (d, J=8.4Hz, 1H), 6.81 (d, J=3.6Hz, 1H),
J=7.6, 1.6Hz, 1H), 7.23 (dd, J=8.0, 1.6Hz, 1H), 7.15 (dd, 6.78 (d, J=16Hz, 1H), 6.63 (d, J=3.6Hz, 1H), 5.81 (s, 1H),
J=8.4, 1.6Hz, 1H), 7.14 (d, J=1.6Hz, 1H), 6.91 (d, J=16Hz, 4.45 (d, J=8.4Hz, 1H), 3.71–3.68 (m, 1H), 3.59–3.54 (m, 1H),
1H), 6.89 (d, J=8.0Hz, 1H), 6.06 (s, 2H), 5.74 (s, 1H), 4.45 2.62–2.59 (m, 1H), 2.31–2.24 (m, 1H), 2.15–2.06 (m, 2H);
(d, J=6.4Hz, 1H), 3.72–3.66 (m, 1H), 3.61–3.54 (m 1H), 13C-NMR (150MHz, acetone-d6) δ: 188.5, 165.6, 162.0, 155.1,
2.56–2.51 (m, 1H), 2.33–2.23 (m, 1H), 2.12–2.06 (m, 2H);13C- 138.0, 133.2, 131.9, 128.6, 127.1, 125.5, 125.1, 125.0, 122.9,
NMR (150MHz, acetone-d6) δ: 189.4, 165.7, 161.5, 150.2, 117.4, 115.4, 93.5, 56.1, 47.5, 27.6, 24.1; IR (ATR); 3012, 1740,
149.4, 140.0, 138.2, 133.2, 131.9, 130.9, 128.5, 127.2, 125.2, 1515, 1462, 1423, 1366, 1218 and 853cm−1; ESI-HR-MS Calcd
124.8, 122.8, 109.2, 107.0, 102.5, 93.2, 56.1, 47.5, 27.6, 24.1; for C40H3479Br2N4NaO6 847.0743 [2M+Na]+; Found 847.0792.
IR (ATR); 2976, 1741, 1644, 1549, 1516, 1465, 1367, 665
(S,Z)-11-((E)-4-(7-Nitro-1H-indol-3-yl)-2-oxobut-3-
and 626cm−1; ESI-HRM Calcd for C23H20N2NaO4 411.1321 en-1-ylidene)-1,2,3,10,11,11a-hexahydro-5H-benzo[e]pyrrolo-
[M+Na]+; Found 411.1272.
(S,Z)-11-((E)-2-Oxo-4-(1H-pyrrol-2-yl)but-3-en-1-ylidene)-
[1,2-a][1,4]diazepin-5-one (10l)
The compound was synthesized according to the general
1,2,3,10,11,11a-hexahydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin- procedure in 7% yield as a yellow pigment.
5-one (10i)
Spectral Data of 10l
1
The compound was synthesized according to the general
[α]D20 +266 (c 0.025, MeOH); H-NMR (600MHz, DMSO-
procedure in 6% yield after ODS purification as a yellow pig- d6) δ: 13.18 (brs, 1H), 12.39 (brs, 1H), 8.59 (d, J=8.2Hz,
ment.
Spectral Data of 10i
1H), 8.21 (d, J=8.2Hz, 1H), 8.09 (s, 1H), 7.83 (d, J=16Hz,
1H), 7.82 (dd, J=8.2, 1.6Hz, 1H), 7.55 (td, J=8.2, 1.6Hz,
[α]D20 +574 (c 0.5, MeOH); H-NMR (400MHz, acetone-d6) 1H), 7.41 (t, J=8.2Hz, 1H), 7.25 (td, J=8.2, 1.2Hz, 1H), 7.17
δ: 13.31 (brs, 1H), 10.67 (brs, 1H), 7.88 (dd, J=8.0, 1.2Hz, (d, J=8.2Hz, 1H), 7.13 (d, J=16Hz, 1H), 5.86 (s, 1H), 4.46
1H), 7.52 (td, J=8.0, 1.2Hz, 1H), 7.51 (d, J=16Hz, 1H), 7.21 (d, J=7.8Hz, 1H), 3.67 −3.63 (m, 1H), 3.53–3.49 (m, 1H),
(td, J=8.0, 1.2Hz, 1H), 7.12 (d, J=8.0Hz, 1H), 7.00 (dd, 3.44–3.38 (m, 1H), 2.22–2.15 (m, 1H), 2.08–2.03 (m, 2H);
J=2.8, 1.6Hz, 1H), 6.62 (d, J=16Hz, 1H), 6.56 (dd, J=3.6, 13C-NMR (150MHz, DMSO-d6) δ: 188.7, 164.7, 159.8, 137.0,
1.6Hz, 1H), 6.21–6.19 (m, 1H), 5.56 (s, 1H), 4.43 (d, J=8.0Hz, 133.3, 133.1, 132.6, 132.0, 130.8, 129.5, 129.2, 128.6, 126.9,
1H), 3.70–3.65 (m, 1H), 3.61–3.54 (m, 1H), 2.52–2.47 (m, 1H), 124.9, 124.0, 122.0, 120.3, 119.6, 114.0, 92.9, 55.1, 46.8, 26.5,
2.31–2.21 (m, 1H), 2.11–2.06 (m, 2H); 13C-NMR (100MHz, 23.2; IR (ATR); 3006, 1739, 1533, 1515, 1451, 1368, 1220
acetone-d6) δ: 189.7, 165.8, 160.6, 138.4, 133.2, 131.9, 130.7, and 846cm−1; ESI-HR-MS Calcd for C24H21N4O4 429.1563
130.3, 128.3, 124.5, 123.3, 122.7, 122.5, 114.5, 111.1, 92.9, 56.0, [M+H]+; Found 429.1604.
1
47.5, 27.6, 24.1; IR (ATR); 3015, 1739, 1547, 1508, 1441, 1368,