Advanced Synthesis & Catalysis
10.1002/adsc.201800278
carbonyl and a variety of di-tertiary glycols. For the
40644078; c) S. Naidoo, V. Jeena, Synthesis 2017,
49, 26212631.
synthesis
of
4-substituted
quinolines
this
methodology is realized by relay actions of
molybdenum and a Lewis acid. In addition, all
products were obtained in good to high yields in short
reaction times taking advantage from the microwave
irradiation technique.
[
[
4] a) J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi,
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Experimental Section
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50825090.
from o-Nitrobenzaldehydes 1 and Glycols 2 Catalyzed
by MoO
2 2
Cl (dmf)
2
In a 10 mL reaction vessel, the corresponding 2-
nitrobenzaldehyde 1 (0.5 mmol) and 1,2-diol 2 (1.1 mmol)
were added to anhydrous DMA (1 mL). Then,
2 2 2
MoO Cl (dmf) (9 mg, 0.025 mmol, 5 mol %) was added
and the vessel was sealed with a septum. The reaction
mixture was stirred for at 180 ºC 2060 min under
microwave heating (maximum wattage: 150 W).
Alternatively, in a screw-cap sealed tube, the mixture of
2 2 2
reagents (using 10 mol % of MoO Cl (dmf) ) was stirred at
1
80 ºC for 2 h (oil bath temperature). After completion of
the reaction, monitored by GC-MS, the mixture was cooled
to rt, diluted with Et O (30 mL), and washed with a 1/1
mixture of 0.3 M aq. NaOH/brine (3 × 10 mL). The
2
2 4
organic layer was dried over anhydrous Na SO and
concentrated under reduced pressure. The residue was
purified by deactivated silica gel flash column
chromatography
(hexane/EtOAc)
to
afford
the
corresponding quinoline 3. When methyl 3-formyl-4-
nitrobenzoate (1g) was employed as starting material, the
addition of p-toluenesulfonic acid monohydrate (PTSA)
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(
95 mg, 0.5 mmol) was also required to obtain the
8
3, 23092316; c) D.W. Tan, H.-X. Li, D.-L. Zhu, H.-
Y. Li, D. J. Young, J.-L. Yao, J.-P. Lang, Org. Lett.
018, 20, 608611; d) S. Parua, R. Sikari, S. Sinha, S.
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corresponding quinoline 3g. Characterization data and
NMR spectra are presented in the Supporting Information.
2
Acknowledgements
2
Chelucci, A. Porcheddu, Chem. Rec. 2017, 17,
200216.
Financial support from Junta de Castilla y León and FEDER
(
BU076U16) and Ministerio de Economía y Competitividad
MINECO) and FEDER (CTQ2016-75023-C2-1-P) is gratefully
(
acknowledged. R. R.-P. thanks Universidad de Burgos for a
predoctoral contract. S. S.-P. thanks Junta de Castilla y León and
FEDER for a postdoctoral contract.
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