F
Z. Lu et al.
Paper
Synthesis
3,5-Diacetyl-2,6-dimethyl-4-(3-nitrophenyl)pyridine (3n)22
Supporting Information
Light yellow solid; yield: 230 mg, 0.74 mmol (63%); mp 124.3–
125.2 °C (Lit.9 126–128 °C).
Supporting information for this article is available online at
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IR (KBr): 2925, 1698, 1533 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.02 (s, 6 H), 2.55 (s, 6 H), 7.59 (dt,
J = 7.6, 1.6 Hz, 1 H), 7.66 (t, J = 8.0 Hz, 1 H), 8.13 (t, J = 1.6 Hz, 1 H),
8.32 (ddd, J = 8.0, 2.0, 1.2 Hz, 1 H).
References
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MS (ESI): m/z = 313.3 [M + 1]+.
3,5-Diacetyl-2,4,6-trimethylpyridine (3o)25
Yellow oil; yield: 220 mg, 1.07 mmol (90%).
IR (KBr): 2925, 1698, 1558 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.12 (s, 3 H), 2.45 (s, 6 H), 2.50 (s, 6 H).
MS (ESI): m/z = 206.3 [M + 1]+.
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2625.
3,5-Diacetyl-2,6-dimethyl-4-isobutylpyridine (3p)
Yellow oil; yield: 223 mg, 0.90 mmol (78%).
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(xii), 9. (d) Montazerozohori, M.; Nasr-Esfahani, M.; Joohari, S.;
Haghighat, N. Asian J. Chem. 2010, 22, 4249.
IR (KBr): 2961, 1699, 1557 cm–1
1H NMR (400 MHz, CDCl3): δ = 0.83 (d, J = 6.8 Hz, 6 H), 1.70–1.77 (m, 1
H), 2.39 (d, J = 7.6 Hz, 2 H), 2.46 (s, 6 H), 2.52 (s, 6 H).
13C NMR (100 MHz, CDCl3): δ = 22.4, 22.7, 29.7, 32.7, 39.1, 135.7,
142.2, 152.2, 205.8.
.
ΗRMS (ESI): m/z [M + H]+ calcd for C15H22NO2: 248.1645; found:
248.1647.
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Dimethyl 2,6-Dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicar-
boxylate (4)26 (Figure 2)
O
N
MeO2C
CO2Me
N
4
Figure 2 Structure of undesired product 4
Light blue solid; yield: 356 mg, 1.08 mmol (92%); mp 94.8–94.9 °C
(Lit.26 93 °C).
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IR (KBr): 2952, 1735, 1560 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 2.67 (s, 6 H), 3.39 (s, 6 H), 6.55 (dd,
J = 8.0, 1.0 Hz, 1 H), 7.44 (ddd, J = 8.0, 7.5, 1.0 Hz, 1 H), 7.52 (dd, J = 7.5,
1.0 Hz, 1 H), 7.72 (td, J = 7.5, 1.0 Hz, 1 H).
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MS (ESI): m/z = 329.3 [M + 1]+.
Acknowledgment
This project was supported by the National Natural Science Founda-
tion of China (No. 21572118), the Natural Science Foundation of
Jiangsu Province (No. BK20130526), the Priority Academic Program
Development of Jiangsu Higher Education Institutions (PAPD) and
Jiangsu University (No. 10JDG042 and No. 14JDG018).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 49, A–G