Synthesis of 2-substituted-1,3-oxazolidines under microwave irradiation

Full text of DOI:10.1134/S1070363207050295

ISSN 1070-3632, Russian Journal of General Chemistry, 2007, Vol. 77, No. 5, p. 969.
Pleiades Publishing, Ltd., 2007.
Original Russian Text
No. 5, p. 875.
D.P. Khrustalev, A.A. Suleimenova, S.D. Fazylov, A.M. Gazaliev, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77,
LETTERS
TO THE EDITOR
Synthesis of 2-Substituted-1,3-oxazolidines
under Microwave Irradiation
D. P. Khrustalev, A. A. Suleimenova, S. D. Fazylov, and A. M. Gazaliev
Institute of Organic Synthesis and Coal Chemistry of Kazakhstan,
ul. Alikhanova 1, Karaganda, 100000 Kazakhstan
e-mail: khrustalev@mail.kz
Received January 15, 2007
DOI: 10.1134/S1070363207050295
2-Substituted-1,3-oxazolidines still remain actively
studied nitrogen-containing heterocycles due to their
effective application in medicine, agriculture, and
polymer and paint and varnish industry [1 2]. Among
fairly few synthetic approaches to 1,3-oxazolidines,
heterocyclization heterocyclization of vicinal amino-
alcohols with various aldehydes and ketones occupies
a special place. Depending on the activity of the start-
ing reagents, the reaction time varies from 4 to 12 h.
The yields of the target products are 65 95% [3 5].
idin-3-yl)ethanol, bp 145 C (5 mm Hg), yield 80%;
2-(2-isopropyloxazolidin-3-yl)ethanol, bp 94 C
(2 mm Hg), yield 83%; 2-(2-sec-butyloxazolidin-3-
yl)ethanol, bp 104 C (3 mm Hg), yield 81%; 2-[2-(4-
methoxyphenyl)oxazolidin-3-yl]ethanol, bp 198 C
(7 mm Hg), yield 85%.
The physical and chemical properties of the listed
compounds were coincident with those reported in [3]
for the compounds were prepared by the procedure in
[5].
We studied the heterocyclization process on an
example of the condensation of diethanolamine with
various aldehydes and ketones without a solvent under
microwave irradiation (MWI).
REFERENCES
1. Spielman, M.A., J. Am. Chem. Soc., 1994, vol. 66,
p. 1244.
H
R
2. Mel’nikov, N.N. and Karkasov, Yu.A., Khimiya ger-
bitsidov i regulyatorov rosta rastenii (Chemistry of
Herbicides and Plant Growth Regulators), Moscow,
1962.
C
H MWI
O
+ O=C
HOC2H4
N
OH
HOC2H4 NH
H2C CH2
H2O
R
3. Khrustalev, D.P., Cand. Sci (Chem.) Dissertation,
To this end, 0.06 mol of diethanolamine and
0.06 mol of the corresponding aldehyde were mixed
in a 250-ml heat-resistant conical flask, and the mix-
ture was placed into a household microwave oven
(70 W). The reaction duration was 10 15 min. The
products were isolated by vacuum distillation.
Karaganda, 2003.
4. Fazylov, S.D., Gazaliev, A.M., and Khrustalev, D.P.,
Zh. Obshch. Khim., 1999, vol. 69, no. 11, p. 1931.
5. Khrustalev, D.P., Fazylov, S.D., and Gazaliev A.M., in
The Problems of Chemistry of the Central Kazakhstan,
Jubilee Collection of Scientific Works, Karaganda,
1998, p. 138.
This procedure was used to synthesize the follow-
ing 2-substituted-1,3-oxazolidines: 2-(2-phenyloxazol-
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