D. J. R. O’Mahony, V. Krchnˇa´k / Tetrahedron Letters 43 (2002) 939–942
Table 1. Purity and yield of quinazolinones
941
Compound
tR (min)
Purity (%)a
Yield (%)b
MW
[M+H]+
7a
7b
7c
7d
7e
7f
4.0
6.6
6.1
4.1
3.7
6.8
7.8
100
87
95
97
100
94
15
11
20
15
19
20
15
400
342
369
364
245
372
326
401.2
343.4
370.2
365.1
246.2
373.1
327.3
7g
100
a Determined at 280 nm.
b Average plate yield.
Acknowledgements
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(e) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.;
Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105,
3709–3710; (f) Kulkarni, Y. D.; Abdi, S. H. R.; Sharma,
V. L. J. Indian Chem. Soc. 1984, 61, 720–721; (g)
Mazurkiewicz, R. Monatsh. Chem. 1989, 120, 973–980;
(h) Ismail, M. F.; Shams, E. I.; Mustafa, O. E. A. Indian
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The authors wish to thank Mr. Michael Kobel for
analytical assistance with the mass spectral measure-
ments, and Drs. Andrew Burritt and Mark Holladay
for comments on the manuscript.
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10. A representative procedure follows: The aldehyde resin
(0.3 mmol) in a 10 mL fritted syringe, reductively ami-
nated with R1 primary amine as previously described,1,7
was acylated with the R2 o-nitro-benzoic acid (3 equiv.),
HOBt (3 equiv.) and DIC (3 equiv.) in DMF (0.9 mL/
syringe). After 16 h, the resin was washed with DMF,
methanol and DCM. The nitro group was reduced to the
aniline with a solution of SnCl2·2H2O (2 M) and DIEA
(1 M) in degassed NMP (4 mL/syringe) for 24 h, then
washed with NMP, NMP/water (2/1), methanol, DMF
and DCM. The resins were transferred to a 96 well plate
(ca. 60 mg/well), and treated with a solution of the acid
(7 equiv.), DIC (3.5 equiv.) and pyridine (7 equiv.) in
dioxane (0.3 mL) for 24 h. After a second coupling, the