Y. Wada, N. Nishida, N. Kurono, T. Ohkuma, K. Orito
FULL PAPER
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3-[2-(Hydroxymethyl)-3,4-(methylenedioxy)phenyl]isoquinoline
(29a): A similar treatment to that described above for 27b of 27a
(31 mg, 0.1 mmol) with Na(OCH2CH2OCH3)2H2 (123 mg,
0.42 mmol, 70% toluene solution) in THF (2 mL) afforded, by an
autooxidation of 28a [30 mg, 1H NMR (270 MHz, CDCl3): δ =
3.83, 4.49, 4.90 (each br. s, each 2 H, 4-H, benzylic H, 1-H), 6.03
(s, 2 H, OCH2O), 6.81 (d, J = 7.9 Hz, 1 H, 5Ј-H), 7.16–7.33 (m, 5
H, 5-, 6-, 7-, 8- and 6Ј-H) ppm], 29a [Rf = 0.35 (3 % MeOH/
CH2Cl2), 16 mg, 0.057 mmol, 57% yield] as colorless crystals, m.p.
1
180–182 °C (EtOAc/hexane). IR (Nujol): ν = 1627, 1583 cm–1. H
˜
NMR (270 MHz, CDCl3): δ = 4.54 (s, 2 H, benzylic CH2), 6.09 (s,
2 H, OCH2O), 6.35 (br. s, 1 H, OH), 6.86, 7.15 (AB type, J =
8.2 Hz, each 1 H, 5Ј- and 6Ј-H), 7.64, 7.75 (each t, J = 8.2 Hz, each
1 H, 6- and 7-H), 7.90 (d, J = 8.2 Hz, 1 H, 5-H), 7.91 (s, 1 H, 4-
H), 8.03 (d, J = 8.2 Hz, 1 H, 8-H), 9.26 (s, 1 H, 1-H) ppm. 13C
NMR (67.5 MHz, CDCl3): δ = 56.42 (t), 101.47 (t), 107.58 (d),
119.70 (d), 122.05 (s), 123.95 (d), 127.18 (d), 127.47 (d), 127.68 (d),
131.07 (d), 134.88 (s), 136.91 (s), 146.91 (s), 147.84 (s), 150.97 (d),
152.59 (s) ppm. EI-MS: m/z = 279 (100) [M]+, 251 (33), 236 (26),
205 (34), 192 (18), 130 (21), 96 (20). C17H13NO3 (279.29): calcd. C
73.11, H 4.69, N 5.02; found C 72.92, H 4.76, N 4.94.
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Asymmetry 1994, 5, 1567–1578; by Pictet–Spengler reaction: h)
[12]
[13]
A similar N-acylation with 2-bromophenylacetyl chloride was
unsuccessful. The reaction with 3-(2-bromophenyl)propanoyl
chloride afforded 2-[3-(2-bromophenyl)propanoyl]-1,2-dihy-
droisoquinoline almost quantitatively, which underwent neither
a Heck cyclization nor a radical cyclization.
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