10.1002/asia.201801450
Chemistry - An Asian Journal
FULL PAPER
ESI-MS positive mode: 364 [M+H]+]+; MS2 (m/z): 349, 333 and 318. ESI-
HRMS: m/z calcd. for [C21H21N3O3+H]+: 364.1646; found 364.1656.
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5: Brown solid; yield: 3.0 mg (0.013 mmol, 50 %); 1H NMR (CDCl3)
δ(ppm) = 6.97 (d, 2H, J=8.4 Hz, H6,6’), 6.88 (d, 2H, J=8.4 Hz, H3,3’), 6.78
(t, 2H, J=8.8 Hz, H5,5’), 6.73 (t, 2H, J=8.8 Hz, H4,4’) and 3.85 (s, 6H, CH3).
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[C14H14N2O2+H]+: 243.1129; found 243.1128.
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6: Brown solid; yield: 2.7 mg (0.0074 mmol, 45 %); 1H NMR (CDCl3)
δ(ppm) = 7.68 (d, 1H, J=8.0 Hz, H17), 7.22 (s, 1H, H4), 7.16 (t, 1H, J=8.0
Hz), 7.05 (m, 3H), 7.01 (d, 2H, J=8.0 Hz), 6.88 (s, 1H, H1), 3.91 (3H,
CH3), 3.85 (3H, CH3) and 3.77 (3H, CH3). 13C{H} NMR (CDCl3) δ(ppm) =
159.9, 153.2, 153.1, 151.9, 149.8, 136.9, 127.9, 125.5, 122.8, 122.1,
121.7, 112.3, 111.6, 97.7 (C1), 91.9 (C4), 56.7(CH3), 56.1(CH3) and 55.9
(CH3).ESI-MS positive mode: 364 [M+H]+; ESI-HRMS: m/z calcd. for
[C21H21N3O3+H]+: 364.1646; found 364.1656.
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7: Dark yellow solid; yield: 5.1 mg (0.0169 mmol, 68 %); 1H-RMN
(Acetone-d6) δ(ppm) = 8.65 (s, 2H, H3,3’), 8.07 (d, 2H, J=9.2 Hz, H5,5’) and
7.06 (d, 2H, J=9.2 Hz, H6,6’). 13C{H} RMN (Acetone-d6) δ(ppm) = 151.5
(C1,1’), 138.5 (C2,2’), 135.1 (C4,4’), 127.7 (C5,5’), 120.9 (C3,3’) and 117.5
(C6,6’). ESI-MS negative mode: 301 [M-H]-; MS2 (m/z): 273; ESI-HRMS:
m/z calcd. for [C12H10N6O4-H]-: 301.0691; found 301.0690.
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Acknowledgements
Funding: This work was supported by the FCT – Fundação para
a Ciência e Tecnologia [Projecto Estratégico UID/QUI/00100/
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2013,PTDC/BBB-EBB/0122/2014,
RECI/QEQQIN/0189/2012
and Projeto Infraestruturas 022125] and Research Unit GREEN-
it "Bioresources for Sustainability" at ITQB [UID/Multi/
04551/20139]. We gratefully acknowledge to Dr. M. Conceição
Oliveira for the helpful discussion about ESI-MS results and the
IST-UL NMR and MS Networks for facilities.
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Keywords: Dyes • Laccase • Biocatalysis • Green synthesis
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