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Journal Name
Organic & Biomolecular Chemistry
DOI: 10.1039/C5OB00458F
yield: 76%; IR (neat) 2935, 1801, 1665, 1465, 1232, 1165 cm-1; 1H
4-(2-Oxo-2-(thiophen-2-yl)ethyl)-3,4-dihydro-2H-indeno[1,2-
o
NMR (300 MHz, CDCl3): δ 2.98 (dd, J = 17.7, 10.2 Hz, 1H), 3.39 b]furan-2-one (10m): Colorless solid; mp 145-146 C, yield: 67%;
(d, J = 24.6 Hz, 1H), 3.64 (dd, J = 17.7, 4.8 Hz, 1H), 3.68 (dd, J = IR (neat) 3106, 2921, 1792, 1722, 1657, 1414, 1387, 1229 cm-1; H
1
24.6, 1.8 Hz, 1H), 4.12 (dd, J = 10.2, 4.8 Hz, 1H) 7.29-7.41 (m, 3H), NMR (300 MHz, CDCl3): δ 2.95 (dd, J = 17.1, 10.2 Hz, 1H), 3.42
7.45-7.48 (m, 3H), 7.89-7.92 (d, J = 8.7Hz, 2H); 13C NMR (75MHz, (d, J = 24.0 Hz, 1H), 3.55-3.70 (m, 2H), 4.12 (dd, J = 10.2, 5.1 Hz,
CDCl3): δ 35.3, 39.9, 40.3, 118.1, 122.3, 123.9, 126.4, 127.5, 129.2, 1H), 7.15 (t, J = 4.5, 1H), 7.30-7.41 (m, 3H), 7.48 (d, J = 7.2 Hz,
129.5, 132.3, 134.7, 140.2, 147.7, 157.3, 177.8, 196.8. Anal Calcd 1H), 7.69-7.71 (m, 2H); 13C NMR (75MHz, CDCl3): δ 34.2, 39.2,
for C19H13ClO3: C, 70.27; H, 4.03. Found: C, 69.98; H, 3.93.
4-(2-(2-Chlorophenyl)-2-oxoethyl)-3,4-dihydro-2H-
39.8, 117.1, 121.3, 123.0, 125.5, 126.6, 127.5, 131.3, 131.4, 133.4,
142.6, 146.7, 156.3, 176.9, 190.0. Anal Calcd for C17H12O3S: C,
indeno[1,2-b]furan-2-one (10h): Yellow gummy solid; yield: 64%; 68.90; H, 4.08; S, 10.82. Found: C, 68.62; H, 4.04; S, 10.65.
7-Methyl-4-(2-oxo-2-(thiophen-2-yl)ethyl)-3,4-dihydro-2H-
1
IR (neat) 2919, 1796, 1704, 1587, 1467, 1431, 1258 cm-1; H NMR
(300 MHz, CDCl3): δ 3.03 (dd, J = 18.0, 10.2 Hz, 1H), 3.49 (d, J = indeno[1,2-b]furan-2-one (10n): Brown solid; mp 119-120 oC,
24.3 Hz, 1H), 3.60 -3.73 (m, 2H), 4.11 (dd, J = 10.2, 4.5 Hz, 1H), yield: 55%; IR (neat) 3093, 2918, 1794, 1718, 1660, 1413, 1228 cm-
1
7.28-7.50 (m, 8H); 13C NMR (75MHz, CDCl3)*: δ 34.2, 39.2, 43.3, 1; H NMR (300 MHz, CDCl3): δ 2.42 (s, 3H) 2.93 (dd, J = 17.1,
117.0, 120.9, 122.8, 125.4, 126.1, 126.4, 128.0, 129.8, 130.1, 131.3, 10.2 Hz, 1H), 3.40 (d, J = 24.6 Hz, 1H), 3.52 -3.67 (m, 2H), 4.07
137.5, 146.4, 156.3, 176.8, 200.2. Anal Calcd for C19H13ClO3: C, (dd, J = 10.2, 4.8 Hz, 1H), 7.09-7.16 (m, 2H), 7.21 (s, 1H), 7.34 (d, J
70.27; H, 4.03. Found: C, 69.99; H, 3.92. *One aromatic carbon is = 7.8 Hz, 1H) 7.68-7.70 (m, 2H); 13C NMR (75MHz, CDCl3): δ
merged with others.
7-Methyl-4-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-
19.7, 33.4, 38.1, 39.2, 117.0, 120.6, 121.8, 125.3, 126.6, 130.5,
132.5, 135.7, 141.8, 143.0, 155.5, 176.2, 189.3. Anal Calcd for
indeno[1,2-b]furan-2-one (10i): Colorless solid; mp 144-145 oC, C18H14O3S: C, 69.66; H, 4.55; S, 10.33. Found: C, 69.34; H, 4.42; S,
yield: 81%; IR (neat) 2917, 1811, 1676, 1446, 1375, 1222, 1185 cm- 10.09.
1; 1H NMR (300 MHz, CDCl3): δ 2.42 (s, 3H) 2.99 (dd, J = 18.0,
(E)-Methyl
3-(2-(5-oxo-4,5-dihydrofuran-2-
10.5 Hz, 1H), 3.38 (d, J = 24.6 Hz, 1H), 3.60 -3.71 (m, 2H), 4.09 yl)phenyl)acrylate (11o): Off-white solid; mp 94-95oC, yield: 54%;
(dd, J = 10.5, 4.8 Hz, 1H), 7.11 (d, J = 7.8 Hz, 1H), 7.21 (s, 1H), IR (neat) 2914, 2117, 1782, 1706, 1634, 1433, 1321, 1170 cm-1; H
1
7.35 (d, J = 7.8 Hz, 1H) 7.46-7.51 (m, 2H) 7.60 (tt, J = 7.5, 1.2 Hz, NMR (300 MHz, CDCl3) δ 3.50 (d, J = 2.4 Hz, 2H), 3.83 (s, 3H),
1H), 7.95-7.97 (m, 2H); 13C NMR (75MHz, CDCl3): δ 21.4, 35.3, 5.56 (t, J = 2.4 Hz, 1H), 6.39 (d, J = 15.9 Hz, 1H), 7.43-7.49 (m,
39.8, 40.4, 118.7, 122.6, 123.5, 127.0, 128.0, 128.8, 132.5, 133.6, 2H), 7.58-7.67 (m, 2H), 8.04 (d, J = 15.9 Hz, 1H); 13C NMR (75
136.4, 137.3, 145.0, 157.1, 178.0, 198.2. Anal Calcd for C20H16O3: MHz, CDCl3): δ 35.1, 51.9, 105.1, 120.6, 127.7, 127.9, 128.5, 129.8,
C, 78.93; H, 5.30. Found: C, 78.72; H, 5.21.
129.9, 133.3, 142.9, 152.0, 167.0, 175.3. Anal Calcd for C14H12O4:
C, 68.85; H, 4.95. Found: C, 68.66; H, 5.06.
7-Chloro-4-(2-oxo-2-p-tolylethyl)-3,4-dihydro-2H-indeno[1,2-
b]furan-2-one (10j): Yellow solid; mp 89-90 oC, yield: 60%; IR
(neat) 2922, 1802, 1694, 1572, 1455, 1223 cm-1; 1H NMR (300
MHz, CDCl3): δ 2.43 (s, 3H), 2.99 (dd, J = 18.0, 10.2 Hz, 1H), 3.40
(d, J = 24.6 Hz, 1H), 3.58 (dd, J = 18.0, 5.1 Hz, 1H), 3.68 (d, J =
24.6 Hz, 1H), 4.12 (dd, J = 10.2, 5.1 Hz, 1H), 7.25- 7.30 (m, 3H),
7.38 (d, J = 8.4 Hz, 2H), 7.85 (d, J = 8.4 Hz, 2H). 13C NMR
(75MHz, CDCl3): δ 21.7, 35.3, 39.9, 40.0, 118.4, 124.5, 124.8,
126.1, 128.2, 129.5, 133.5, 133.8, 133.9, 144.7, 146.2, 156.1, 177.3,
197.3. Anal Calcd for C20H15ClO3: C, 70.90; H, 4.46. Found: C,
70.61; H, 4.35.
Acknowledgements
Financial support from the Department of Science and
Technology, DST (No. SB/FT/CS-006/2013) and the Council
of Scientific and Industrial Research, CSIR (No.
02(0219)/14/EMR-II) is gratefully acknowledged.
Notes and references
a
Organic Synthesis Group, Department of Chemistry, School of Chemical
and Biotechnology, SASTRA University, Thanjavur 613401, Tamil Nadu,
India. E-mail: vsridharan@scbt.sastra.edu, vesridharan@gmail.com
4-(2-(Naphthalen-2-yl)-2-oxoethyl)-3,4-dihydro-2H-
indeno[1,2-b]furan-2-one (10k): Colorless solid; mp 114-115 C,
o
b
yield: 80%; IR (neat) 2917, 1792, 1663, 1602, 1391, 1267, 1172,
1036 cm-1; 1H NMR (300 MHz, CDCl3): δ 3.17 (dd, J = 17.7, 10.5
Hz, 1H), 3.43 (d, J = 24.6 Hz, 1H), 3.71 (d, J = 24.6 Hz, 1H), 3.80
(dd, J = 17.7, 4.5 Hz, 1H), 4.20 (dd, J = 10.5, 4.5 Hz, 1H), 7.29-7.43
(m, 3H), 7.52-7.65 (m, 3H), 7.89-7.95 (m, 3H) 8.05 (dd, J = 8.4, 1.5
Hz, 1H), 8.46 (s, 1H); 13C NMR (75MHz, CDCl3): δ 35.4, 40.3,
40.5, 118.2, 122.7, 123.7, 124.1, 126.5, 127.2, 127.6, 128.0, 128.9,
129.0, 129.7, 130.1, 132.5, 132.6, 133.8, 135.9, 148.1, 157.4, 178.1,
198.2. HRMS (ESI): calcd for C23H16NaO3, m/z 363.0997
([M+Na]+); found, m/z 363.0992.
Departamento de Química Orgánica y Farmacéutica, Facultad de
Farmacia, Universidad Complutense, 28040 Madrid, Spain.
c The Institute of Scientific and Industrial Research (ISIR), Osaka University,
Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan
Electronic Supplementary Information (ESI) available: Starting material
synthesis and copies of spectra of products. See DOI: 10.1039/b000000x/
1. For a recent review on structure and activity of strigolactones, see: B.
Zwanenburg and T. Pospíšil, Mol. Plant, 2013, 6, 38.
4-(2-(Furan-2-yl)-2-oxoethyl)-3,4-dihydro-2H-indeno[1,2-
b]furan-2-one (10l): Colorless solid; mp 111-112 oC, yield: 60%; IR
(neat) 3011, 1810, 1701, 1633, 1341, 1177, 1043 cm-1; 1H NMR
(300 MHz, CDCl3): δ 2.89 (dd, J = 17.4, 10.2 Hz, 1H), 3.42 (d, J =
24.9 Hz, 1H), 3.52 (dd, J = 17.4, 5.1 Hz, 1H), 3.64 (dd, J = 24.9, 1.8
Hz, 1H), 4.09 (dd, J = 10.2, 5.1 Hz, 1H) 6.57 (dd, J = 3.6, 1.8 Hz,
1H), 7.23 (d, J = 3.6 Hz, 1H), 7.29-7.40 (m, 3H), 7.47 (d, J = 7.2 Hz,
1H), 7.61 (d, J = 0.9 Hz, 1H); 13C NMR (75MHz, CDCl3): δ 35.1,
39.8, 39.9, 112.5, 117.6, 118.0, 122.1, 123.9, 126.4, 127.4, 132.3,
146.8, 147.7, 152.3, 157.3, 177.8, 187.2. Anal Calcd for C17H12O4:
C, 72.85; H, 4.32. Found: C, 72.52; H, 4.21.
2. For selected references, see: a) C. Ruyter-Spira, W. Kohlen, T.
Charnikhova, A. van Zeijl, L. van Bezouwen, N. de Ruijter, C. Cardoso,
J. A. Lopez-Raez, R. Matusova, R. Bours, F. Verstappen and H.
Bouwmeester, Plant Physiol., 2011, 155, 721; (b) E. Foo and N. W.
Davies, Planta, 2011, 234, 1073; (c) Y. Kapulnik, P.-M. Delaux, N.
Resnick, E. Mayzlish-Gati, S. Wininger, C. Bhattacharya, N. Sejalon-
Delmas, J.-P. Combier, G. Becard, E. Belausov, T. Beeckman, E. Dor, J.
Hershenhorn and H. Koltai, Planta, 2011, 233, 209; (d) M. J. Soto, M.
Fernandez-Aparicio, V. Castellanos-Morales, J. M. Garcia-Garrido, J. A.
Ocampo, M. J. Delgado and H. Vierheilig, H. Soil Biol. Biochem., 2010,
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