10.1002/ejoc.201801884
European Journal of Organic Chemistry
FULL PAPER
CDCl3): δ = 8.31 (dd, J = 7.8, 0.6 Hz, 1H, arom.), 7.98 (dd, J = 7.9, 1.7 Hz,
1H, arom.), 7.70–7.68 (m, 1H, arom.), 7.51–7.43 (m, 2H, arom.), 7.41–
7.32 (m, 1H, arom. + -CH- sp2), 7.07 (td, J = 7.6, 1.1 Hz, 1H, arom.), 7.03
(d, J = 8.3 Hz, 1H, arom.), 3.97 (s, 3H, -OCH3). Spectral data are in good
agreement with literature values.[33]
3-cyclopropyl-1H-isochromen-1-one (2k). Eluent for chromatography:
hexane/EtOAc 9:1. Colorless oil. 1H-NMR (300 MHz, CDCl3):δ = 8.19 (ddd,
J = 8.0, 1.3, 0.7 Hz, 1H, arom.), 7.63 (td, J = 7.7, 1.4 Hz, 1H, arom.), 7.38
(ddd, J = 8.0, 7.4, 1.2 Hz, 1H, arom.), 7.30 (d, J = 7.9 Hz, 1H, arom.), 6.28
(s, 1H, -CH- sp2), 1.79 (tt, J = 8.3, 8.3, 5.1, 5.1 Hz,1H, -CH- sp3), 1.09–
1.01 (m, 2H, -CH2- sp3), 0.95–0.87 (m, 2H, -CH2- sp3). Spectral data are
in good agreement with literature values.[29e]
3-(3-hydroxyphenyl)-1H-isochromen-1-one
(2d).
Eluent
for
chromatography: hexane/EtOAc 6:4. Dark-red solid. 1H-NMR (300 MHz,
d6-acetone): δ = 8.64 (s, 1H, -OH), 8.22 (dd, J = 7.9, 0.6 Hz, 1H, arom.),
7.89–7.75 (m, 1H, arom.), 7.68 (d, J = 7.7 Hz, 1H, arom.), 7.63–7.53 (m,
1H, arom.), 7.45–7.39 (m, 2H, arom.), 7.35 (dd, J = 11.7, 4.5 Hz, 1H,
arom.), 7.28 (s, 1H, -CH- sp2), 7.00–6.91 (m, 1H, arom.). Spectral data are
in good agreement with literature values.[33]
3-Cyclopentyl-1H-isochromen-1-one (2l). Eluent for chromatography:
hexane/EtOAc 9:1. Orange oil. 1H-NMR (300 MHz, CDCl3): δ = 8.23 (d, J
= 8.0 Hz, 1H, arom.), 7.70–7.60 (m, 1H, arom.), 7.46–7.37 (m, 1H, arom.),
7.33 (d, J = 7.8 Hz, 1H, arom.), 6.26 (s, 1H, -CH- sp2), 2.91 (quint, J = 7.9
Hz, 1H, -CH- sp3), 2.08–1.92 (m, 2H, -CH2- sp3), 1.86–1.61 (m, 6H, -CH2-
sp3). Spectral data are in good agreement with literature values.[50]
3-(4-(Dimethylamino)phenyl)-1H-isochromen-1-one (2e). Eluent for
chromatography: hexane/EtOAc 8:2. Yellow solid. 1H-NMR (300 MHz,
CDCl3): δ = 8.26 (d, J = 7.7 Hz, 1H, arom.), 7.76 (d, J = 9.1 Hz, 2H, arom.),
7.63 (m, 1H, arom.), 7.43–7.37 (m, 2H, arom.), 6.73 (m, 3H, 2 arom. + -
CH- sp2), 3.03 (s, 6H, -N(CH3)2). Spectral data are in good agreement with
literature values.[30d]
3-(tert-Butyl)-1H-isochromen-1-one (2m). Eluent for chromatography:
hexane/EtOAc 9:1. Pale yellow oil. H-NMR (300 MHz, CDCl3): δ = 8.25
(d, J = 7.9 Hz, 1H, arom.), 7.67 (td, J = 7.9, 1.5 Hz, 1H, arom.), 7.45 (td, J
= 7.8, 1.5 Hz, 1H, arom.), 7.38 (d, J = 7.8 Hz, 1H, arom.), 6.30 (s, 1H, -
CH- sp2), 1.33 (s, 10H, -(CH3)3). Spectral data are in good agreement with
literature values.[51]
1
3-(thiophen-3-yl)-1H-isochromen-1-one
(2f).
Eluent
for
chromatography: hexane/EtOAc 9:1. White solid. 1H-NMR (300 MHz,
CDCl3): δ = 8.30 (d, J = 7.4 Hz, 1H, arom.), 7.89 (dd, J = 2.9, 1.3 Hz, 1H,
arom.), 7.72 (td, J = 7.7, 1.3 Hz, 1H, arom.), 7.55–7.37 (m, 4H, arom.),
6.79 (s, 1H, -CH- sp2). Spectral data are in good agreement with literature
values.[33]
3-(4-Chlorophenyl)-1H-isochromen-1-one
chlorobenzylidene)isobenzofuran-1(3H)-one
(2n)
(3n).
and
Eluent
3-(4-
for
chromatography: hexane/EtOAc 9:1. Compounds 2n and 3n were only
partially separable by column chromatography. Despite a lot of different
attempts with many eluent mixtures they are always isolated as mixtures.
White solid. 2n: 1H-NMR (300 MHz, CDCl3): δ = 8.30 (d, J = 7.8 Hz, 1H,
arom.), 7.80 (d, J = 8.7 Hz, 2H, arom.), 7.71 (td, J = 7.6, 1.2 Hz, 1H, arom.),
7.50 (t, J = 7.7 Hz, 1H, arom.), 7.42 (d, J = 8.7 Hz, 2H, arom.), 6.92 (s, 1H,
-CH- sp2). 2n + 3n: 1H-NMR (300 MHz, CDCl3): δ = 8.30 (d, J = 7.8 Hz,
1H, arom. of 2n), 7.87–7.78 (m, 2H, arom. of 2n), 7.87 (d, J = 7.8 Hz, 1H,
arom. of 3n), 7.73 (td, J = 7.6, 1.2 Hz, 1H, arom. of 2n), 7.70 (d, J = 8.8
Hz, 2H, arom. of 3n), 7.68 (m, 1H, arom. of 3n), 7.54 (m, 1H, arom. of 3n),
7.53 (d, J = 7.8 Hz, 1H, arom. of 3n), 7.51 (t, J = 7.7 Hz, 2H, arom. of 2n),
7.47–7.40 (m, 2H, arom. of 2n), 7.30 (d, J = 8.8 Hz, 2H, arom. of 3n), 6.93
(s, 1H, -CH- sp2 of 2n), 6.30 (s, 1H, -CH- sp2 of 3n). Spectral data of
compounds [52] are in good agreement with literature values.
2-(p-Tolyl)-4H-benzo[f]isochromen-4-one
(2g).
Eluent
for
chromatography: hexane/EtOAc 9:1. Yellow solid. mp 187.7-188.8 °C. 1H-
NMR (300 MHz, CDCl3): δ = 8.39 (d, J = 8.6 Hz, 1H, arom.), 8.21 (d, J =
8.7 Hz, 1H, arom.), 7.96–7.78 (m, 4H, arom.), 7.75–7.64 (m, 2H, arom.),
7.62 (s, 1H, -CH- sp2), 7.29 (d, J = 8.0 Hz, 2H, arom.), 2.42 (s, 3H, -CH3).
13C-NMR (75 MHz, CDCl3): δ = 162.7 (C=O), 155.1 (C arom.), 140.6 (C
arom.), 136.9 (C arom.), 136.0 (C arom.), 129.6 (CH arom.), 129.32 (C
arom.), 129.27 (CH arom.), 128.9 (CH arom.), 128.1 (CH arom.), 127.8 (C
arom.), 127.2 (CH arom.), 125.4 (CH arom.), 124.2 (CH arom.), 124.0 (CH
arom.), 117.3 (C arom.), 96.7 (CH sp2), 21.4 (-CH3). MS ESI (+): m/z (%)
= 287.5 [M+1]+ (100); C20H14O2 [286.33]. Anal. Calcd for C20H14O2: C,
83.90; H, 4.93. Found: C, 83.71; H, 4.90.
3-(3-(Trifluoromethyl)phenyl)-1H-isochromen-1-one (2o) and 3-(3-
(trifluoromethyl)-benzylidene)isobenzofuran-1(3H)-one (3o). Eluent
for chromatography: hexane/EtOAc 9:1. Compounds 2o and 3o are not
separable by column chromatography. Despite a lot of different attempts
with many eluent mixtures they are always isolated as mixtures. White
solid. 1H-NMR (300 MHz, CDCl3): δ = 8.32 (d, J = 8.2 Hz, 1H, arom. of 2o),
8.12 (s, 1H, arom. of 2o), 8.09 (m, 1H, arom. of 3o), 8.05 (d, J = 7.8 Hz,
1H, arom. of 2o), 7.96-7.93 (m, 2H, arom. of 3o), 7.74 (m, 1H, arom. of 2o
and m, 2H, arom. of 3o), 7.67 (d, J = 7.8 Hz, 1H, arom. of 2o), 7.59 (d, J =
7.8 Hz, 1H, arom. of 2o), 7.54 (m, 2H, arom. of 2o and m, 3H, arom. of
3o), 7.01 (s, 1H, -CH- sp2 of 2o), 6.41 (s, 1H, -CH- sp2 of 3o). 13C-NMR
(75 MHz, CDCl3): δ = 166.6 (C=O of 3o), 161.8 (C=O of 2o), 151.9 (C arom.
of 2o), 145.8 (C arom. of 3o), 141.4 (q, 2J(C,F) = 33 Hz, 1C, C-CF3 of 2o),
140.1 (C arom. of 3o), 136.9 (C arom. of 2o), 135.1 (CH arom. of 2o),
134.6 (CH arom. of 3o), 133.9 (C arom. of 3o), 132.9 (CH arom. of 3o),
132.7 (C arom. of 2o), 131.1 (q, 2J(C,F) = 32 Hz, 1C, C-CF3 of 3o), 130.3
(CH arom. of 3o), 129.8 (CH arom. of 2o), 129.5 (CH arom. of 2o), 129.3
(CH arom. of 3o), 128.7 (CH arom. of 2o), 128.3 (CH arom. of 2o), 126.5
(q, 3J(C,F) = 3.9 Hz, 1C, CH-C-CF3 of 3o), 126.4 (q, 3J(C,F) = 3.8 Hz, 1C,
CH-C-CF3 of 2o), 126.2 (CH arom. of 2o), 125.7 (CH arom. of 3o), 125.6
(C, arom. of 3o), 124.7 (q, 3J(C,F) = 3.8 Hz, 1C, CH-C-CF3 of 3o), 122.0
5-(4-Methoxyphenyl)-7H-thieno[2,3-c]pyran-7-one (2h). Eluent for
chromatography: hexane/EtOAc 8:2. Pale green solid. 1H-NMR (300 MHz,
CDCl3): δ = 7.85–7.77 (m, 3H, arom.), 7.20 (d, J = 5.1 Hz, 1H, arom.), 7.01
(s, 1H, -CH- sp2), 6.97 (d, J = 9.0 Hz, 2H, arom.), 3.87 (s, 3H, -OCH3).
Spectral data are in good agreement with literature values.[33]
7-(4-Methoxyphenyl)-5H-pyrano[4,3-b]pyridin-5-one (2i). Eluent for
chromatography: hexane/EtOAc 1:1. Yellow solid. 1H-NMR (300 MHz,
CDCl3): δ = 8.88 (dd, J = 4.7, 1.8 Hz, 1H, arom.), 8.53-8.39 (m, 1H, arom.),
7.83 (d, J = 9.0 Hz, 2H, arom.), 7.35 (dd, J = 8.0, 4.7 Hz, 1H, arom.), 7.07
(s, 1H, -CH- sp2), 6.97 (d, J = 9.0 Hz, 2H, arom.), 3.85 (s, 3H, -OCH3).
Spectral data are in good agreement with literature values.[45]
3-Propyl-1H-isochromen-1-one (2j). Eluent for chromatography:
hexane/EtOAc 95:5. Colorless oil. 1H-NMR (300 MHz, CDCl3): δ = 8.26 (d,
J = 7.9 Hz, 1H, arom.), 7.68 (td, J = 7.9, 1.2 Hz, 1H, arom.), 7.45 (td, J =
7.8, 0.8 Hz, 1H, arom.), 7.36 (d, J = 7.8 Hz, 1H, arom.), 6.27 (s, 1H, -CH-
sp2), 2.51 (t, J = 7.5 Hz, 2H, -CH2- sp3), 1.75 (sex, J = 7.8 Hz, 2H, -CH2-
sp3), 1.00 (t, J = 7.4 Hz, 3H, -CH3). Spectral data are in good agreement
with literature values.[33]
3
(q, J(C,F) = 3.9 Hz, 1C, CH-C-CF3 of 2o), 120.7 (C, arom. of 2o), 120.3
1
(q, J(C,F) = 272 Hz, 1C, CF3 of 3o), 120.0 (CH arom. of 3o), 120.0 (q,
1J(C,F) = 272 Hz, 1C, CF3 of 2o), 105.2 (-CH- sp2 of 3o), 102.9 (-CH- sp2
This article is protected by copyright. All rights reserved.