FULL PAPERS
Synthesis of Quinazolinones from Alcohols
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performed using a Heracus CHN-O-Rapid analyzer.
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General Procedure for the Oxidation of 2,3-Dihydro-
quinazolin-4(1H)-ones 5a–m to Quinazolinones (6a–
m)
To a magnetically stirred solution of 2,3-dihydroquinazolin-
4(1H)-one 5 (1.0 mmol) in a citrate buffer (0.1M, pH 4.5,
10 mL) under O2, were added HBT (30 mg, 0.2 mmol) and
laccase from T. versicolor (100 U, 20 mg), and the reaction
mixture was stirred at 458C for the time given in Table 4.
Then, the reaction mixture was extracted with ethyl acetate
(3ꢁ15 mL), and the organic layer was dried over anhydrous
Na2SO4. The crude product was purified by silica gel column
chromatography using hexane/ethyl acetate (75:25) as
a mobile phase.
General Procedure for the One-Pot Synthesis of
Quinazolinones (6a–m)
To
a magnetically stirred solution of benzyl alcohol
1 (1.0 mmol) in a citrate buffer (0.1M, pH 4.5, 10 mL) under
O2, were added HBT (30 mg, 0.2 mmol) and laccase from T.
versicolor (200 U, 40 mg), and the reaction mixture was
stirred at 458C. Then, isatoic anhydride 2 (1 mmol), amine 3
(1 mmol) were added, and the mixture was stirred until the
substrates were fully consumed, which was indicated by
TLC. Next, 100 U laccase under O2 were added, and the re-
action mixture was extracted with ethyl acetate (3ꢁ15 mL).
The organic layer was dried over anhydrous Na2SO4, and
the crude product was purified by silica gel column chroma-
tography using hexane/ethyl acetate (75:25) as a mobile
phase.
Analytical data for 2-phenylquinazolin-4(3H)-one (6a):
white solid; mp 133–1358C; (lit.,[34] 128–1298C); 1H NMR
(300 MHz, CDCl3): d=8.34 (d, J=7.7 Hz, 1H), 7.75–7.78
(m, 2H), 7.49–7.57 (m, 6H), 3.51 (s, 3H); 13C NMR
(75 MHz, CDCl3): d=162.74, 156.16, 147.34, 135.41, 134.35,
130.1, 128.93, 128.01, 127.53, 126.03, 126.7, 120.5, 34.3; anal.
calcd. (%) for C15H12N2O: C 76.25, H 5.12, N 11.86; found:
C 76.17, H 4.97, N 11.94.
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Acknowledgements
This work was supported financially by the Biotechnology
Research Center, Tehran University of Medical Sciences,
Tehran, Iran to M.A.F. (grant No. 92-02-90-23628).
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