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Organic & Biomolecular Chemistry
Page 7 of 9
DOI: 10.1039/C7OB00205J
Journal Name
Thereafter, the crude mixture was washed with Et2O to obtain (Hellma, 104F-QS, 10
ARTICLE
×
4 mm, Chamber volume 3.5 mL) was
the desired product (32 mg, 0.098 mmol, 98 %) as a yellow added NaBH4 (2.34 mg, 10 eq.). Emission spectra (upon an
solid, mp = 223-225 °C. IR (ATR): νmax: 3415( H), 1653(CN), excitation at 366 nm in PBS 7.4 at 25 °C) were recorded before
1597 (CO). 1H NMR (300 MHz, DMSO-d6): δ = 3.61 (s, 3H), 3.67 and after the addition of NaBH4.
(s, 3H), 3.81 (s, 3H), 5.66 (s, 1H), 6.39 (s, 1H), 6.89-6.95 (m, 2H),
7.25-7.32 (m, 3H), 7.37 (d, J = 6.0 Hz, 1H), 7.48 (d, J = 6.0 Hz,
1H) ppm. 13C NMR (75 MHz, DMSO-d6): δ = 29, 55.5, 55.6,
65.2, 110.8, 111, 115.7, 118.9, 120, 127.4, 127.5, 128.2, 130.3,
132.3, 152.9, 155.4, 156.2, 160.6 ppm. HRMS (ESI+): calcd. for
C18H19N2O4 [M+H]+ 327.1345; found 327.1344.
Acknowledgements
We thank the Region Haute-Normandie (FEDER CHIMBIO
HN0001401) for financial support to K.R. This work was also
partially supported by Rouen University, INSA Rouen, Rouen
University, the Centre National de la Recherche Scientifique
(CNRS), and the Labex SynOrg (ANR-11-LABX-0029). The
authors are grateful to Mrs Amna Benzarti and Miss Nadia
Msaddek, NMR service at the Faculty of Monastir, University
of Monastir for the NMR analysis and to the Ministry of Higher
Education and Scientific Research of Tunisia for financial
support (LR11ES39). The authors also thank Albert Marcual
(CNRS) for HRMS analyses, Patricia Martel (University of
Rouen-Normandie) for IR analyses.
7-Methoxy-3-((2-methoxyphenyl)(prop-2-yn-1-
yloxy)methyl)-1-methylquinoxalin-2(1H)-one 6. To a solution
of
5 (32 mg, 0.1 mmol) in DMF (2 ml) was added NaH (3 mg,
1.2 eq.) at room temperature. After stirring the mixture for 10
min, the propargyl bromide (9 µl, 0.12 mmol, 1.2 eq.) was
added and the reaction was heated at 60 °C for 6 h.
Thereafter, the crude mixture was extracted with
water/dichloromethane, before removing the solvent under
reduced pressure. The crude material was purified by flash
column chromatography on silica gel (Cyclohexane/EtOAc from
100:0 to 50:50) to obtain the desired product
6 (19 mg, 0.5
1
mmol, 50 %) as a yellow solid, mp = 171-173 °C. H NMR (300
MHz, DMSO-d6): δ = 3.41 (s, 1H), 3.60 (s, 3H), 3.75 (s, 3H), 3.83
(s, 3H), 4.27 (s, 2H), 6.45 (s, 1H), 6.93-7.02 (m, 2H), 7.25-7.30
(m, 4H), 8.49 (d, J= 6.0 Hz, 1H) ppm. 13C NMR (75 MHz, DMSO-
d6): δ = 29.0, 55.6, 56.9, 71.7, 77.2, 80.3, 111.1, 115.7, 119.5,
120.1, 126.5, 127.3, 127.8, 129.1, 132.4, 153, 155.4, 156.8,
157.7 ppm. HRMS (ESI+): calcd. for C21H21N2O4 [M+H]+
365.1501; found 365.1512.
Notes and references
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3-(((1-(2-cholesterolethyl)-1H-1,2,3-triazol-4-
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6
(18 mg, 0.05 mmol) and cholesterol azide 741 (35 mg, 0.075
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5
M. Weïwer, J. Spoonamore, J. Wei, B. Guichard, N. T. Ross, K.
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6
7
8
desired product
8 (31 mg, 0.038 mmol, 76% yield) as a yellow
solid, mp = 160-162 °C. 1H NMR (300 MHz, DMSO-d6): δ =
0.84-1.49 (m, 30H), 1.74-2.24 (m, 11H), 3.61 (s, 3H), 3.71 (s,
3H), 3.78 (s, 2H), 3.81 (s, 3H),4.46 (s, 2H), 4.59-4.68 (m, 2H),
6.42 (s, 1H), 6.94-7.01 (m, 2H), 7.23-7.39 (m, 4H), 7.48 (d, J =
6.0Hz, 1H), 8.06 (s, 1H) ppm. 13C NMR (75 MHz, DMSO-d6): δ =
18.5, 18.9, 20.5, 22.3, 22.6, 23.2, 23.8, 27.4, 27.7, 27.8, 29,
31.3, 31.3, 35.1, 35.6, 36.1, 45.7, 49.5, 49.7, 55.5, 55.6, 56.1,
63.1, 65.6, 65.7, 72.3, 78.3, 78.4, 111, 111.2, 115.7, 119.4,
120.1, 121.1, 123.7, 124.4, 126.9, 127.3, 127.7, 128.8, 132.4,
140.2, 143.7, 153.1, 155.4, 156.7, 158.1 ppm. HRMS (ESI+):
calcd. for C50H70N5O5 [M+H]+ 820.5394; found 820.5393.
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