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New Journal of Chemistry
Page 4 of 6
DOI: 10.1039/C6NJ03103J
ARTICLE
Journal Name
In this way, we chose the 2-phenylacyl-benzo[1,3-d]selenazole mixture was cooled to room temperature, quenched with
3a to react with NaBH4 to generate the corresponding saturated solution of Na2S2O3 (20 mL) and the reaction was
secondary alcohol
4 in 99% yield after 12 h. Still, compound 3a extracted with ethyl acetate (3x 20 mL). The combined organic
was allowed to react with butylmagnesium bromide in THF to phase was dried over anhydrous MgSO4 and concentrated
produce the corresponding tertiary alcohol
(Scheme 4).
5
in 70% yield under reduced pressure. The residue was purified by
chromatography on silica gel using hexane as eluent to provide
3a-l
.
Conclusions
Acknowledgements
In summary, we have described a simple and efficient strategy
for synthesizing unprecedented 2-acyl-benzo[1,3-d]selenazoles
using aryl methyl ketones and bis(2-aminophenyl) diselenide.
The use of a conventional heating method was explored to
synthesize the benzo[1,3-d]selenazoles in moderate to
excellent yields (33–94%) after 48 hours. On the other hand,
microwave irradiation was shown to be more efficient in terms
of time and energy economy, enabling us to prepare the
benzo[1,3-d]selenazoles in good to excellent yields (60–94%)
We thank the CNPq (Universal 474963/2013-6), FAPERGS (PqG
002070-2551/13-3, PRONEM 16/2551-0000240-1 and ARD
16/2551-0000358-0), CAPES and FINEP for financial support.
References
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(phenylmethanone)benzo[1,3-d]selenazole was shown to be
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secondary and tertiary alcohol benzo[1,3-d]selenazole
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bar, the aryl methyl ketone 1a-l (0.70 mmol) was dissolved in
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eluent to provide 3a-l
.
General Procedure for the Synthesis of 2-acyl-benzo[1,3-
d]selenazole 3a-l under Microwave Irradiation
In a 10 mL glass vial equipped with a magnetic stir bar, the aryl
methyl ketone 1a-l (0.70 mmol) was dissolved in DMSO (1.5
mL) and molecular iodine (0.7 mmol) was added. The reaction
mixture was left to stir at 100 °C (measured with an IR sensor
on the outer surface of the reaction vial) for about 20 minutes
(to in situ formation of 2-arylethan-1,2-dione 1’a-l) under
microwave irradiation (irradiation power of 200 W and the
6
7
ramp temperature rate was
aminophenyl) disselenide
3
min). After this, bis(2-
2
(0.25 mmol) and sodium
metabisulfite (0.50 mmol) were added, and the reaction was
maintained for 2 hours at 100 °C. After this time, the reaction
4 | J. Name., 2012, 00, 1-3
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