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ARTICLE
DOI: 10.1039/C8MD00315G
1
triethyl phosphate were heated at 120
℃
for 10h. The excess Yellow solid, yield 76%. H NMR (400 MHz, DMSOꢀ
d
6) δ
triethyl phosphate was removed in vacuum and the crude 8.05 (d,
J
= 7.6 Hz, 1H), 7.86 (d,
J
= 8.8 Hz, 1H), 7.48ꢀ7.66 (m,
product was purified by silica gel column chromatography 3H), 7.36 (s, 1H), 7.32 (d,
J
= 8.4 Hz, 1H), 7.22 (d, J = 8.8 Hz,
(EtOAc/petroleum ether) to give 14a
,
14b or 14c compound as 1H), 7.08 (d,
J = 8.4 Hz, 1H), 6.99 (d, J = 8.4 Hz, 1H), 6.72 (d,
oil.
J
= 8.8 Hz, 1H), 4.50 (t, 2H), 3.83 (s, 6H), 3.71 (t, 2H), 3.29 (s,
3H).
General procedure for the preparation of 15
(E)ꢀ5ꢀ(3,4ꢀdimethoxystyryl)ꢀ6ꢀ(2ꢀmethoxyethoxy)ꢀN,Nꢀ
dimethylnaphthalenꢀ2ꢀamine (15f)
Sodium methoxide (3 mmol) was added to a solution of
phosphonic acid diethyl ester 14a, 14b or 14c (1 mmol) in dry
1
DMF (2 mL). The resulting mixture was stirred at room Yellow solid, yield 61%. H NMR (400 MHz, DMSOꢀ
d
6) δ
temperature for 5 min, and compounds
2
,
6
,
10a or 10b (1.2 7.88 (d,
J
= 8.7 Hz, 1H), 7.48ꢀ7.50 (m, 2H), 7.34 (s, 1H), 7.30
mmol) was added at 0°C. The mixture was stirred at room (d,
J
= 8.6 Hz, 1H), 7.20 (d, J = 8.8 Hz, 1H), 6.79ꢀ6.99 (m, 3H),
temperature for 0.5 h and then for 12 h at 80°C. The reaction 6.70 (d,
J = 8.8 Hz, 1H), 4.52 (t, 2H), 3.82 (s, 6H), 3.74 (t, 2H),
was quenched by pouring into iceꢀwater with stirring. Reactions 3.30 (s, 3H), 3.06(s, 6H).
that gave solids were filtered and dried. Reactions that gave oils
(E)ꢀ5ꢀ(3,4ꢀdimethoxystyryl)ꢀ6ꢀ(2ꢀmethoxyethoxy)naphthalenꢀ2ꢀol
(15g)
were extracted with ethyl acetate, and the ethyl acetate layer
was washed with water and brine and then dried over Na2SO4.
1
Filtration and evaporation of the solvent afforded the oils. The Yellow solid, yield 68%. H NMR (400 MHz, DMSOꢀ
d
6) δ
= 8.6 Hz, 1H),, 7.34 (s, 1H),
= 8.8 Hz, 1H), 7.19 (s, 1H),
= 8.8 Hz,
crude solids or oils were purified by flash chromatography on 7.96 (d,
silica gel with petrol / ethyl acetate as the elution solvent to 7.32 (d,
J
J
J
= 9.2 Hz, 1H), 7.52 (d,
= 8.4 Hz, 1H), 7.22 (d,
= 8.6 Hz, 1H), 6.94ꢀ6.99 (m, 2H), 6.77 (d,
J
J
afford the desired product 15a
ꢀ
15l
.
7.03 (d,
J
1H), 4.42 (t, 2H), 3.82 (s, 6H), 3.75 (t, 2H), 3.31 (s, 3H).
(E)ꢀ1ꢀ(3,5ꢀdimethoxystyryl)ꢀ2ꢀ(methoxymethoxy)naphthalene
(15a)
(E)ꢀ8ꢀ(3,4ꢀdimethoxystyryl)ꢀ7ꢀ(2ꢀmethoxyethoxy)naphthalenꢀ2ꢀol
1
(15h)
Yellow solid, yield 88%. H NMR (400 MHz, DMSOꢀ
d
6) δ
1
8.09 (d,
3H), 7.20 (d,
1H), 6.87 (s, 1H), 6.72 (d,
J
= 9.1 Hz, 1H), 7.92 (d,
= 8.6 Hz, 1H), 7.08 (d,
= 8.6 Hz, 1H), 6.21 (s, 1H), 4.61 (t, 2H), 7.21 (d,
J
= 8.6 Hz, 1H), 7.44ꢀ7.65 (m, Yellow solid, yield 64%. H NMR (400 MHz, DMSOꢀ
d
6) δ
J
J
= 8.3 Hz, 1H), 6.92 (s, 7.79 (d,
J
= 9.2 Hz, 1H), 7.62 (d,
J
= 8.6 Hz, 1H), 7.32ꢀ7.35 (m,
J
J
= 8.8 Hz, 1H), 7.15 (d, J = 8.6 Hz, 1H), 6.87ꢀ
2H), 3.85 (s, 6H), 3.68 (t, 2H), 3.31 (s, 3H).
6.96 (m, 3H), 6.74 (d, J = 8.8 Hz, 1H), 4.50 (t, 2H), 3.83 (s,
6H), 3.71 (t, 2H), 3.29 (s, 3H).
(E)ꢀ5ꢀ(3,5ꢀdimethoxystyryl)ꢀ6ꢀ(2ꢀmethoxyethoxy)ꢀN,Nꢀ
dimethylnaphthalenꢀ2ꢀamine (15b)
(E)ꢀ2ꢀ(2ꢀmethoxyethoxy)ꢀ1ꢀ(4ꢀmethoxystyryl)naphthalene (15i)
1
Yellow solid, yield 61%. 1H NMR (400 MHz, DMSOꢀ
d
6) δ7.82 Yellow solid, yield 64%. H NMR (400 MHz, DMSOꢀ
d
6) δ
(d,
7.04 (d,
J
= 8.6 Hz, 1H), 7.44ꢀ7.50 (m, 2H), 7.18 (d,
J
= 8.7 Hz, 1H), 7.75ꢀ7.85 (m, 5H), 7.58ꢀ7.54 (m, 1H), 7.24ꢀ7.38 (m, 3H), 7.20
(d, = 8.6 Hz, 1H), 7.03 (d, = 8.6 Hz, 1H), 6.79 (d, = 8.2
J
= 8.3 Hz, 1H), 6.90 (s, 1H), 6.85 (s, 1H), 6.67 (d,
J
=
J
J
J
8.6 Hz, 1H), 6.78 (s, 1H), 6.19 (s, 1H), 4.60 (t, 2H), 3.83 (s, Hz, 1H), 4.43 (t, 2H), 3.82 (s, 3H), 3.70 (t, 2H), 3.39 (s, 3H).
6H), 3.65 (t, 2H), 3.29 (s, 3H), 3.13 (s, 6H).
(E)ꢀ6ꢀ(2ꢀmethoxyethoxy)ꢀ5ꢀ(4ꢀmethoxystyryl)ꢀN,Nꢀ
(E)ꢀ5ꢀ(3,5ꢀdimethoxystyryl)ꢀ6ꢀ(2ꢀmethoxyethoxy)naphthalenꢀ2ꢀol dimethylnaphthalenꢀ2ꢀamine (15j)
(15c)
1
Yellow solid, yield 51%. H NMR (400 MHz, DMSOꢀd6) δ
1
Yellow solid, yield 73%. H NMR (400 MHz, DMSOꢀ
8.01 (d,
8.8 Hz, 1H), 7.12 (s, 1H), 7.08 (d,
6.95 (s, 1H), 6.84 (s, 1H), 6.71 (d,
4.59 (t, 2H), 3.84 (s, 6H), 3.62 (t, 2H), 3.30 (s, 3H).
d
6) δ 7.68ꢀ7.74 (m, 3H), 7.54ꢀ7.57 (m, 2H), 7.23 (d,
= 8.3 Hz, 1H), 7.19 (d, J = 7.11ꢀ7.15 (m, 2H), 6.55ꢀ6.59 (m, 2H), 6.78 (d,
= 8.3 Hz, 1H), 7.02 (s, 1H), 4.41 (t, 2H), 3.82 (s, 3H), 3.74 (t, 2H), 3.40 (s, 3H), 2.99(s, 6H).
J
J
= 9.2 Hz, 1H),
= 9.2 Hz, 1H),
J
= 9.2 Hz, 1H), 7.65 (d,
J
J
J
= 8.8 Hz, 1H), 6.24 (s, 1H),
(E)ꢀ6ꢀ(2ꢀmethoxyethoxy)ꢀ5ꢀ(4ꢀmethoxystyryl)naphthalenꢀ2ꢀol
(15k)
Yellow solid, yield 45%. H NMR (400 MHz, DMSOꢀ
7.72ꢀ7.79 (m, 3H), 7.67 (d, = 8.6 Hz, 1H), 7.43 (s, 1H), 7.25
(E)ꢀ8ꢀ(3,5ꢀdimethoxystyryl)ꢀ7ꢀ(2ꢀmethoxyethoxy)naphthalenꢀ2ꢀol
(15d)
1
d
6) δ
J
1
Yellow solid, yield 51%. H NMR (400 MHz, DMSOꢀ
7.80 (d,
d
6) δ (d,
(d,
J
J
= 9.2 Hz, 1H), 7.14ꢀ7.19 (m, 2H), 6.87ꢀ6.92 (m, 2H), 6.80
= 9.2 Hz, 1H), 4.44 (t, 2H), 3.83 (s, 3H), 3.76 (t, 2H), 3.38
J
= 8.4 Hz, 1H), 7.60 (d,
J
= 8.6 Hz, 1H), 7.20 (d,
J
=
8.8 Hz, 1H), 7.01ꢀ7.12 (m, 3H), 6.90 (s, 1H), 6.85 (s, 1H), 6.74 (s, 3H).
(d, = 8.8 Hz, 1H), 6.18 (s, 1H), 4.60 (t, 2H), 3.85 (s, 6H), 3.65
J
(E)ꢀ7ꢀ(2ꢀmethoxyethoxy)ꢀ8ꢀ(4ꢀmethoxystyryl)naphthalenꢀ2ꢀol
(15l)
(t, 2H), 3.28 (s, 3H).
(E)ꢀ1ꢀ(3,4ꢀdimethoxystyryl)ꢀ2ꢀ(2ꢀmethoxyethoxy)naphthalene
(15e)
1
Yellow solid, yield 49%. H NMR (400 MHz, DMSOꢀ
d
6) δ
7.74ꢀ7.80 (m, 3H), 7.69 (d,
J = 9.0 Hz, 1H), 7.49 (s, 1H), 7.22
6 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 2012