Supporting information
Choline hydroxide: an efficient and biocompatible basic catalyst for the synthesis of
biscoumarins under mild conditions
Anlian Zhu, Shukun Bai, Lingjun Li, Mingyue Wang, Jianji Wang*
School of Chemistry and Chemical Engineering, Collaborative Innovation Center of
Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of
Green Chemical Media and Reactions, Ministry of Education, Henan Normal
University, Xinxiang, Henan 453007, P. R. China
Telephone: +86-0373-3325805; Fax: +86-0373-3329030
[email protected]
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H-NMR spectra were recorded on a BRUKER AV-400 instrument at room
temperature. Chemical shifts () are expressed in ppm from the internal standard
tetramethylsilane and coupling constants (J) are given in Hz.
3a. 3,3′-(Phenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
OH
O
OH
O
O
O
White crystalline solid; H NMR (400 MHz, CDCl3): δ 6.27 (s, 1H, CH); 7.12-8.08
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(m, 13H, Ar-H).
3b. 3,3′-(4-Fluorophenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
F
OH
O
OH
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.23 (s, 1H, CH); 6.88-8.07 (m,
12H, Ar-H).
3c. 3,3′-(4-Chlorophenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
Cl
OH
OH
O
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.22 (s, 1H, CH); 7.14-8.07 (m,
12H, Ar-H).
3d. 3,3′-(4-Bromophenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
Br
OH
OH
O
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.20 (s, 1H, CH); 7.15-8.07 (m,
12H, Ar-H).
3e. 3,3′-(4-Hydroxylphenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
OH
OH
O
OH
O
O
O
White crystalline solid; 1H NMR (400 MHz, DMSO-d6): δ 6.15 (s, 1H, CH);
6.54-7.81 (m, 12H, Ar-H).
3f. 3,3′-(2-Hydroxylphenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
OH
OH
OH
O
O
O
O
Yellow crystalline solid; 1H NMR (400 MHz, DMSO-d6): δ 6.15 (s, 1H, CH);
6.56-7.80 (m, 12H, Ar-H).
3g. 3,3′-(4-Nitrophenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
NO2
OH
O
OH
O
O
O
Light yellow crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.34 (s, 1H, CH);
7.20-8.03 (m, 12H, Ar-H).
3h. 3,3′-(3-Nitrophenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
NO2
OH
O
OH
O
O
O
Light yellow crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.34 (s, 1H, CH);
7.20–8.03 (m, 12H, Ar-H).
3i. 3,3′-(2-Nitrophenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
NO2
OH
OH
O
O
O
O
Yellow crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.53 (s, 1H, CH); 7.18-8.01
(m, 12H, Ar-H).
3j. 3,3′-(4-Methylphenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
CH3
OH
OH
O
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3H, CH3); 6.22 (s, 1H,
CH); 7.01-8.08 (m, 12H, Ar-H).
3k. 3,3′-(4-Trifluoromethylphenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
CF3
OH
OH
O
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.31 (s, 1H, CH); 7.20-8.06 (m,
12H, Ar-H).
3l. 3,3′-(4-Methoxyphenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
OCH3
OH
O
OH
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 3.73 (s, 3H, CH3O); 6.21 (s,
1H, CH); 6.74-8.16 (m, 12H, Ar-H).
3m. 3,3′-(4-Hydroxy-3-methoxyphenylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
OH
OCH3
OH
OH
O
O
O
O
Light yellow crystalline solid; 1H NMR (400 MHz, DMSO-d6): δ 3.53 (s, 3H, OCH3);
6.16 (s, 1H, CH); 6.51-7.82 (m, 11H, Ar-H).
3n. 3,3′-(N-pyridylmethylene)bis-(4-hydroxy-2H-chromen-2-one)
N
OH
OH
O
O
O
O
White crystalline solid; 1H NMR (400 MHz, CDCl3): δ 6.25 (s, 1H, CH); 7.06-8.28 (m,
12H, Ar-H).
3o. 3,3′-(2- Furanyl)bis-(4-hydroxy-2H-chromen-2-one)
O
OH
O
OH
O
O
O
Brown solid; H NMR (400 MHz, CDCl3): δ 5.98 (s, 1H, CH); 6.14-6.26(m, 3H,
1
3×CH ); 7.19-8.10 (m, 8H, Ar-H).
3p. 3,3′-(3,4-Piperonyl)bis-(4-hydroxy-2H-chromen-2-one)
O
O
OH
OH
O
O
O
O
White solid; H NMR (400 MHz, CDCl3): δ 5.84 (s, 2H, CH2); 6.18 (s, 1H, CH);
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6.63-8.08 (m, 11H, Ar-H).