10.1002/ejoc.201601582
European Journal of Organic Chemistry
FULL PAPER
2p (35 mg, 18 %) was isolated as white solid (mp= 266-268 oC).
1H NMR (300 MHz, DMSO-d6): δ=11.72 (s, 1H), 7.54 (d, J = 9.3
Hz, 1H), 7.36 – 7.11 (m, 8H), 7.02 (dd, J = 7.7, 1.9 Hz, 2H), 6.45
(d, J = 9.2 Hz, 1H). 13C NMR (100 MHz, DMSO-d6): δ=162.3 (Cq),
145.9 (Cq), 143.4 (CH), 138.1 (Cq), 134.8 (Cq), 129.7 (CH), 129.4
(ddd, J = 8.4, 7.1, 1.4 Hz, 1H), 7.49 (ddd, J = 8.1, 7.1, 1.2 Hz, 1H),
7.40 (dd, J = 8.2, 0.7 Hz, 1H), 7.25 (t, J =7.7 Hz, 1H, ovewrlaps
with CDCl3 signal), 7.18 (t, J = 7.9 Hz, 1H), 6.89 (dt, J = 7.7, 1.2
Hz, 1H), 6.85 (ddd, J = 8.5, 2.7, 0.9 Hz, 1H), 6.83 – 6.77 (m, 3H),
6.74 (dd, J = 2.7, 1.5 Hz, 1H), 3.71 (s, 3H), 3.63 (s, 3H). 13C NMR
(CH), 128.7 (CH), 128.2 (CH), 128.0 (CH), 126.4 (CH), 121.8 (CH), (100 MHz, CDCl3): δ= 162.8 (Cq), 159.8 (Cq), 159.4 (Cq), 138.7
118.8 (Cq). HRMS (ESI/TOF) calcd. for C17H14NO [M+H]+
248.1075, found 248.1080.
(Cq), 137.3 (Cq), 136.9 (Cq), 136.4 (Cq), 132.8 (CH), 129.6 (CH),
129.6 (CH), 127.6 (CH), 126.8 (CH), 125.9 (CH), 125.3 (Cq),
124.4 (CH), 121.4 (CH), 117.4 (CH), 117.1 (Cq), 115.4 (CH),
114.3 (CH), 113.2 (CH), 55.4 (OCH3), 55.3 (OCH3). HRMS
(ESI/TOF) calcd. for C23H20NO3 [M+H]+ 358.1443, found
358.1451.
3,4-Bis(4-methoxyphenyl)isoquinolin-1(2H)-one
(2q).
Prepared by analogy to compound 2a from N-acyl sulfonamide
1.8b (150 mg, 0.50 mmol), 1,2-bis(4-methoxy-phenyl)-ethyne
(240 mg, 1.01 mmol), 3,5-dinitrobenzoic acid potassium salt (37.9
mg, 0.15 mmol) and [Ru(cymene)Cl2]2 (30.9 mg, 0.05 mmol) in
7.5 mL of t-butanol. Crude product was purified by column
chromatography on silica gel (Hex:EtOAc 3:1-1:1) to yield 2q (175
mg, 97%) as a brownish solid (mp= 261-264 oC).
1H NMR (400 MHz, DMSO-d6): δ=11.40 (s, 1H), 8.29 (dd, J = 7.9,
1.1 Hz, 1H), 7.61 (ddd, J = 8.4, 7.1, 1.5 Hz, 1H), 7.48 (ddd, J =
8.1, 7.0, 1.2 Hz, 1H), 7.16 (d, J = 8.7 Hz, 3H), 7.05 (d, J = 8.7 Hz,
2H), 6.87 (d, J = 8.7 Hz, 2H), 6.78 (d, J = 8.8 Hz, 2H), 3.74 (s, 3H),
3.71 (s, 3H).13C NMR (100 MHz, DMSO-d6): δ=161.8 (Cq), 158.9
(Cq), 158.0 (Cq), 138.6 (Cq), 138.4 (Cq), 132.8 (CH), 132.3 (),
131.1 (CH), 128.0 (Cq), 127.0 (Cq), 126.7 (CH), 125.9 (CH),
124.9 (CH), 124.8 (Cq), 114.7 (Cq), 113.7 (CH), 113.1 (CH), 55.0
(OCH3), 54.9 (OCH3). Analytical data are in accordance with
those reported in the literature.[4e]
3,4-Bis(3-bromophenyl)isoquinolin-1(2H)-one (2t). Prepared
by analogy to compound 2a from N-acylsulfonamide 1.8b (150
mg, 0.50 mmol), 1,2-bis(3-bromophenyl)ethyne (339 mg, 1.01
mmol), 3,5-dinitrobenzoic acid potassium salt (37.9 mg, 0.15
mmol) and [Ru(cymene)Cl2]2 (30.9 mg, 0.05 mmol) in 7.5 mL of t-
butanol. Crude product was purified by column chromatography
on silica gel (Hex:Acetone 3:1 – 1:1) to yield 2t (142 mg, 62%) as
an off-white solid. (mp= 258-262 oC). 1H NMR (400 MHz, DMSO-
d6): δ=11.66 (s, 1H), 8.32 (dd, J = 8.0, 1.4 Hz, 1H), 7.68 (ddd, J =
8.4, 7.1, 1.5 Hz, 1H), 7.55 (ddd, J = 8.2, 7.2, 1.2 Hz, 1H), 7.52 –
7.45 (m, 3H), 7.42 (t, J=1.7 Hz, 1H), 7.30 (t, J = 7.7 Hz, 1H), 7.26
– 7.17 (m, 3H), 7.13 (d, J = 8.1 Hz, 1H). 13C NMR (100 MHz,
DMSO-d6): δ= 161.6 (Cq), 138.0 (Cq), 137.5 (Cq), 137.4 (Cq),
136.4 (Cq), 134.2 (CH), 132.8 (CH), 132.6 (CH), 131.3 (CH),
130.9 (CH), 130.4 (CH), 130.2 (CH), 129.8 (CH), 129.0 (CH),
126.9 (CH), 126.6 (CH), 125.1 (Cq), 124.8 (CH), 121.4 (Cq),
120.9 (Cq), 114.5 (Cq). HRMS (ESI/TOF) calcd. for C21H14Br2NO
[M+H]+ 453.9442, found 453.9440
3,4-Bis(4-(trifluoromethyl)phenyl)isoquinolin-1(2H)-one (2r)
Prepared by analogy to compound 2a from N-acylsulfonamide
1.8b (150 mg, 0.50 mmol), 1,2-bis(4-(trifluoromethyl)phenyl)
ethyne (317 mg, 1.01 mmol), 3,5-dinitrobenzoic acid potassium
salt (37.9 mg, 0.15 mmol) and [Ru(cymene)Cl2]2 (30.9 mg, 0.05
mmol) in 7.5 mL of t-butanol. Crude product was purified by
crystallization from i-PrOH to yield 2r (191 mg, 87 %) as a white
solid (mp= 266-268 oC).1H NMR (400 MHz, DMSO-d6): δ=11.76
(s, 1H), 8.35 (dd, J = 8.0, 1.0 Hz, 1H), 7.70 – 7.65 (m, 3H), 7.63
(d, J = 8.2 Hz, 2H), 7.57 (ddd, J = 8.2, 7.1, 1.2 Hz, 1H), 7.49 (d, J
= 7.9 Hz, 2H), 7.43 (d, J = 7.8 Hz, 2H), 7.11 (d, J = 8.2 Hz, 1H).
13C NMR (100 MHz, DMSO-d6): δ= 161.6 (Cq), 140.0 (Cq), 138.2
(Cq), 137.6 (Cq), 137.3 (Cq), 132.9 (CH), 132.7 (CH), 130.9 (CH),
128.7 (Cq, q, J = 31.8 Hz), 127.8 (Cq, q, J = 31.9 Hz), 127.0 (CH),
126.9 (CH),125.22 (Cq), 125.19 (CH, q, J=3.5 Hz), 124.77 (CH),
124.69 (CH, q, J = 4.0 Hz), 124.2 (Cq, q, J=271.2 Hz), 123.9 (Cq,
q, J=272.2 Hz), 114.73 (Cq). 19F NMR (376 MHz, DMSO-d6): δ= -
61.02 (s), -61.22 (s).HRMS (ESI/TOF) calcd. for C23H14F6NO
[M+H]+ 434.0980, found 434.0971.
3,4-Dipropylisoquinolin-1(2H)-one (2u). Prepared by analogy
to compound 2a from N-acylsulfonamide 1.8b (150 mg, 0.50
mmol), 4-octyne (148 μL, 111 mg, 1.01 mmol), 3,5-dinitrobenzoic
acid potassium salt (37.9 mg, 0.15 mmol) and [Ru(cymene)Cl2]2
(30.9 mg, 0.05 mmol) in 7.5 mL of t-butanol. Crude product was
purified by crystallization from i-PrOH to yield 2u (100 mg, 86%)
as light yellowish solid (mp > 170 oC(dec.)).
1H NMR (400 MHz, CDCl3): δ=10.86 (br s, 1H), 8.46 (br s, 1H),
7.77 – 7.62 (m, 2H), 7.43 (br s, 1H),2.78 – 2.62 (m, 4H), 1.75 (dq,
J = 13.7, 6.7, 6.3 Hz, 2H), 1.60 (dq, J = 14.9, 7.4 Hz, 2H), 1.10 –
1.01 (m, 6H). 13C NMR (100 MHz, CDCl3): δ= 163.8 (Cq), 138.8
(Cq), 137.9 (Cq), 132.4 (CH), 127.8 (CH), 125.5 (CH), 123.3 (Cq),
113.3 (Cq), 33.2 (CH2), 28.6 (CH2), 23.9 (CH2), 22.9 (CH2), 14.5
(CH3), 14.1 (CH3). Analytical data are in accordance with those
reported in the literature.
3,4-Bis(3-methoxyphenyl)isoquinolin-1(2H)-one
(2s).
4-Methyl-3-phenylisoquinolin-1(2H)-one (2v) and 3-methyl-4-
phenylisoquinolin-1(2H)-one (2v’). Prepared by analogy to
compound 2a from N-acylsulfonamide 1.8b (150 mg, 0.50 mmol),
1-phenyl-1-propyne (126 μL, 117 mg, 1.01 mmol), 3,5-
dinitrobenzoic acid potassium salt (37.9 mg, 0.15 mmol) and
[Ru(cymene)Cl2]2 (30.9 mg, 0.05 mmol) in 7.5 mL of t-butanol.
Crude product was purified by column chromatography on silica
gel (DCM:Hex:EtOAc 1:4:1-1:1:1) to yield a mixture of 2v and 2v’
Prepared by analogy to compound 2a from N-acylsulfonamide
1.8b (150 mg, 0.50 mmol), 1,2-bis(3-methoxyphenyl)ethyne (240
mg, 1.01 mmol), 3,5-dinitrobenzoic acid potassium salt (37.9 mg,
0.15 mmol) and [Ru(cymene)Cl2]2 (30.9 mg, 0.05 mmol) in 7.5 mL
of t-butanol. Crude product was purified by column
chromatography on silica gel (Hex:Acetone 3:1 – 1:1) to yield 2s
o
1
(103 mg, 57%) as a solid oil. (mp= 161-165 C). H NMR (400
MHz, CDCl3): δ= 9.58 (s, 1H), 8.46 (dd, J = 8.0, 1.5 Hz, 1H), 7.59
1
(2:1, 113 mg, 95%) as light yellowish solid. H NMR (300 MHz,
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