Facile one-pot synthesis of oxazolidin-2-ones from phenyl 2-hydroxyalkyl selenides

Article abstract of DOI:10.1080/00397910701465420

A novel, convenient, efficient, three-step, one-pot synthesis of 2-oxazolidinones from phenyl 2-hydroxyalkyl selenides was developed. Using this methodology, 2-oxazolidinones are obtained in good yields (76-85%) by reaction of phenyl 2-hydroxyalkyl seleni

Full text of DOI:10.1080/00397910701465420

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Facile One‐Pot Synthesis of Oxazolidin‐2‐ones
from Phenyl 2‐Hydroxyalkyl Selenides
Shou‐Ri Sheng a , Hai‐Rong Luo a , Zhen‐Zhong Huang a , Wu‐Kang Sun a
Xiao‐Ling Liu a
&
a College of Chemistry and Chemical Engineering, Jiangxi Normal
University , Nanchang, China
Published online: 14 Aug 2007.
To cite this article: Shou‐Ri Sheng , Hai‐Rong Luo , Zhen‐Zhong Huang , Wu‐Kang Sun & Xiao‐Ling Liu
(2007) Facile One‐Pot Synthesis of Oxazolidin‐2‐ones from Phenyl 2‐Hydroxyalkyl Selenides, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 37:16,
2693-2699, DOI: 10.1080/00397910701465420
To link to this article: http://dx.doi.org/10.1080/00397910701465420
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Synthetic Communicationsw, 37: 2693–2699, 2007
Copyright # Taylor & Francis Group, LLC
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910701465420
Facile One-Pot Synthesis of
Oxazolidin-2-ones from Phenyl
2-Hydroxyalkyl Selenides
Shou-Ri Sheng, Hai-Rong Luo, Zhen-Zhong Huang,
Wu-Kang Sun, and Xiao-Ling Liu
College of Chemistry and Chemical Engineering, Jiangxi Normal
University, Nanchang, China
Abstract: A novel, convenient, efficient, three-step, one-pot synthesis of 2-oxazolidi-
nones from phenyl 2-hydroxyalkyl selenides was developed. Using this methodology,
2-oxazolidinones are obtained in good yields (76–85%) by reaction of phenyl 2-hydro-
xyalkyl selenides with benzoyl isocyanate and subsequent oxidation/cyclization,
followed by hydrolysis with hydrochloric acid solution.
Keywords: one-pot synthesis, 2-oxazolidinones, phenyl 2-hydroxyalkyl selenide
Oxazolidin-2-ones are a very interesting class of compounds because of their
various pharmacological effects,[1] and some molecules containing the 2-oxa-
zolidinone moieties have shown antibacterial activity.[2] Recently, they have
also found application as synthetic intermediates, mainly in synthetic
organic chemistry as chiral auxiliaries.[3] A survey of the literature reveals a
variety of both natural and unnatural starting points for the preparation of oxa-
zolidinones including the reaction of diols with isocyanates, epoxide
openings, amino acids, aziridines, oxetanes, 2-oxazolones, hydroxy acids or
esters, and perhaps the most common, amino alcohols.[4] Tingoli et al.[5]
Received in Japan October 16, 2006
Address correspondence to Shou-Ri Sheng, College of Chemistry and Chemical
Engineering, Jiangxi Normal University, Nanchang 330027, China. E-mail:
shengsr@jxnu.edu.cn
2693

2694
S.-R. Sheng et al.
previously developed a synthetic procedure for oxazolidin-2-ones from vicinal
carbamate selenides promoted by PhSeOTf. Although the synthetic routes to
oxazolidinones are well documented, efforts are continuing for the develop-
ment of more efficient methods with experimental simplicity. Phenyl b-hydro-
xyalkyl selenides are a class of valuable selenium intermediates in organic
synthesis among many organoselenium reagents;[6] they can be converted to
allylic alcohols, olefins, bomohydrins, vinyl selenides, epoxide, tetrahydro-
furan derivatives, and some other important natural products. As part of an
ongoing research program focused on the use of phenyl b-hydroxyalkyl
selenides in organic synthesis,[7] we report herein a novel, convenient,
efficient, three-step, one-pot preparation of 2-oxazolidinones from phenyl
2-hydroxyalkyl selenides (Scheme 1).
Phenyl 2-hydroxyalkyl selenides 1 could be easily obtained by the
reaction of benzeneselenolate ions with the corresponding epoxides[8] in
ethanol at ambient temperature in moderate to good yield. With
compounds 1 in hand, we examined the synthesis of target compounds 4.
First of all, phenyl 2-hydroxy-2-phenylethyl selenide (1a) as starting
material was reacted with benzoyl isocyanate in THF at room temperature
for 16 h to give phenyl 2-[(benzoylamino)carbonyl]oxy-2-phenylethyl
selenide (2a) in 92% yield. Reaction of benzoyl isocyanate (326 mg,
2.2 mmol) with phenyl 2-hydroxy-2-phenylethyl selenide (554 mg,
2.0 mmol) at room temperature continued until the starting alcohol was
completely consumed. Then the solvent was evaporated and the crude
product was purified by column chromatography on silica gel with ether/
n-hexane (6:4) as eluent to afford phenyl 2-[(benzoylamino)carbonyl]oxy-
2-phenylethyl selenide (2a) in 92% yield. 1H NMR: d (CDCl3) ¼ 8.12
(s, 1H, NH), 7.85–7.80 (m, 2H), 7.61–7.42 (m, 8H), 7.34–7.08 (m, 5H),
4.60 (dd, J ¼ 8.2, 5.3 Hz, 1H), 3.22 (dd, J ¼ 12.4, 8.2 Hz, 1H), 3.13 (dd,
J ¼ 12.4, 5.3 Hz, 1H). 13C NMR (CDCl3): d ¼ 165.1 (CO), 147.53 (CO),
35.4. (CH2), 80.9 (CH), 117.1, 118.7, 126.6, 127.0, 127.5, 128.5, 128.9,
130.9, 132.0, 132.7, 134.4, 141.2. IR (neat): n ¼ 3272, 1756, 1734, 1505,
1182, 1056, 965 cm21. Anal. calcd. for C22H19NO3Se: C, 62.27; H, 4.51;
N, 3.30. Found: C, 62.33; H, 4.60; N, 3.33. Treatment of 2a with an
excess of m-chloroperbenzoic acid (MCPBA) in THF in the presence of
Scheme 1. Reaction conditions: (a) BzNCO, THF, rt, 15–17 h; (b) MCPBA,
K2HPO4, THF, rt, 6–8 h; (c) 4 N HCl, 658C, 4 h.

Oxazolidin-2-ones
2695
potassium hydrogenphosphate afforded the corresponding selenone inter-
mediate 3a; subsequently an intramolecular cyclization reaction occurred
easily because of the great leaving ability of the selenonyl group. Without
further isolation, 4 N HCl was added to the reaction mixture and stirred
at 658C for 4 h to afford the corresponding 5-phenyl-oxazolidin-2-one 4a
in 85% yield. After a series of experiments, we have found it most con-
venient to carry out the three-step reaction successively in one pot, giving
almost the same yield even though selenide intermediates 2a and cyclized
product of 3a can be isolated and purified by chromatography. With our suc-
cessfull initial studies of the preparation of 4a, extension of this method to
the synthesis of other analogues in moderate to good yields was investigated
(Table 1). The water-soluble potassium benzeneseleninate was obtained as a
by-product, which can acidified with concd. HCl and subsequently reduced
with hydrazine monohydrate to recover diphenyl diselenide in moderate
yield for the preparation of starting material phenyl 2-hydroxyalkyl
selenides. The alkaline aqueous solution containing potassium benzenesele-
ninate was neutralized with concd. HCl and then acidified by further
addition of the acid. The resulting suspension was evaporated, and the
residue was suspended in MeOH (20 mL). Hydrazine monohydrate
(3.5 mmol, 0.16 mL) was added gradually to the suspension. Stirring
continued until diphenyl diselenide was formed, as indicated by the
yellow color. The mixture was then concentrated in vacuo, poured into
water (30 mL), and extracted with Et2O (320 mL). The organic layer was
dried over anhydrous sodium sulfate and evaporated. Diphenyl diselenide
was recovered as a pure compound in about 60% yield.
In summary, we have described a novel, convenient, three-step, one-pot
ester-oxidation/cyclization-hydrolysis procedure for the conversion of
phenyl 2-hydroxyalkyl selenides to oxazolidin-2-ones in moderate to good
yield.
Table 1. One-pot synthesis of substituted oxazolidin-2-ones from phenyl 2-hydro-
xyalkyl selenides
Entry
R1, R2 (phenyl 2-hydroxyalkyl selenide 1)
Product
Yield (%)a
1
2
3
4
5
6
7
8
H, C6H5
H, C6H5CH2
H, C6H5OCH2
4a
4b
4c
4d
4e
4f
85
82
85
83
82
81
81
76
H, C6H5CH2OCH2
H, 4-CH3C6H4OCH2
H, CH3
H, C2H5
(2-hydroxycyclohexyl phenyl selenide)
4g
4h
aIsolated yield based on phenyl 2-hydroxyalkyl selenides 1.

2696
S.-R. Sheng et al.
EXPERIMENTAL
Melting points were uncorrected. 1H NMR (400 MHz) and 13C NMR (100 MHz)
spectra were recorded on a Bruker Avance (400-MHz) spectrometer, using
CDCl3 as the solvent and TMS as internal standard. IR spectra were taken on
a Perkin-Elmer SP One FT-IR spectrophotometer. Mass spectra (EI, 70 eV)
were recorded on a HP5989B mass spectrometer. Microanalyses were
performed with a Perkin Elmer (PE) 2400 elemental analyzer. Styrene oxide,
3-phenylpropylene oxide, 1,2-epoxybutane, cyclohexene oxide, and propylene
oxide were commercially available, and the other two epoxides were prepared
according to the literature procedure.[9] Diphenyl diselenide,[10] phenyl 2-hydro-
xyalkyl selenides (1a,[11] 1c,[8] 1d,[8] 1e,[7] and 1h;[12] 1b, 1f, and 1gare unknown
compounds) were synthesized according to literature methods.[8] THF was
distilled under N2 from sodium/benzophenone immediately prior to use.
Other reagents were obtained from commercial suppliers and used without
further purification. All reactions were monitored by thin-layer chromatography
(TLC).
Data
2-Hydroxy-3-phenylpropyl phenyl selenide (1b): Light yellow oil (yield:
1
85%); H NMR: d ¼ 7.51–7.48 (m, 2H), 7.32–7.21 (m, 8H), 3.96–3.94
(m, 1H), 3.30 (dd, J ¼ 12.4, 7.8 Hz, 1H), 3.16 (dd, J ¼ 12.4, 5.6 Hz, 1H),
3.11 (dd, J ¼ 14.1, 6.0 Hz, 1H), 2.94 (dd, J ¼ 14.1, 6.7 Hz, 1H), 2.87 (bs,
1H). 13C NMR: d ¼ 138.2, 135.1, 130.8, 129.3, 128.7, 128.2, 127.0, 119.7,
77.0, 40.6, 35.2. IR (neat): n ¼ 3400, 3050, 2927, 1575, 1478, 1180, 1043,
945, 732, 690 cm21. Anal. calcd. for C15H16OSe: C, 61.86; H, 5.54. Found:
C, 61.88; H, 5.58.
2-Hydroxypropyl phenyl selenide (1f): Light yellow oil (yield: 84%);
1H NMR: d ¼ 7.54–7.48 (m, 2H), 7.27–7.21 (m, 3H), 4.06–4.01 (m, 1H),
3.11 (dd, J ¼ 12.3, 5.2 Hz, 1H), 3.02 (dd, J ¼ 12.3, 6.6 Hz, 1H), 2.83 (br,
1H), 1.45 (d, J ¼ 6.3 Hz, 3H); 13C NMR: d ¼ 135.6, 129.0, 128.2, 126.8,
77.2, 35.3, 20.8; IR (neat): n ¼ 3400, 3052, 2927, 2875, 1580, 1478, 1375,
1180, 1043, 945, 732, 670 cm21. Anal. calcd. for C9H12OSe: C, 50.24; H,
5.62. Found: C, 50.27; H, 5.68.
2-Hydroxybutyl phenyl selenide (1g): Light yellow oil (yield: 86%);
1H NMR: d ¼ 7.55–7.47 (m, 2H), 7.29–7.22 (m, 3H), 4.05–3.99 (m, 1H),
3.13 (dd, J ¼ 12.4, 5.5 Hz, 1H), 3.05 (dd, J ¼ 12.4, 6.8 Hz, 1H), 2.86 (br,
1H), 1.87–1.65 (m, 2H), 1.02 (t, J ¼ 7.0 Hz, 3H); 13C NMR: d ¼ 135.7,
129.2, 128.2, 126.5, 77.1, 35.3, 27.8, 8.8; IR (neat): n ¼ 3400, 3053, 2927,
2872, 1580, 1478, 1378, 1182, 1045, 943, 736, 669 cm21. Anal. calcd. for
C10H14OSe: C, 52.41; H, 6.16. Found: C, 52.46; H, 6.21.

Oxazolidin-2-ones
2697
General Procedure for the Preparation of Oxazolidin-2-ones 4a–4h
Under a nitrogen atmosphere, benzoyl isocyanate (326 mg, 2.2 mmol) was
added to a solution of phenyl 2-hydroxyalkyl selenide (2.0 mmol) in
anhydrous THF (20 mL), and the reaction mixture was stirred at room temp-
erature until TLC analysis indicated that the starting alcohol was completely
consumed (15–17 h). Then the reaction mixture was treated with meta-
chloroperoxybenzoic acid (1.38 g, 8.0 mol) and potassium hydrogenpho-
sphate (1.69 g, 10.0 mmol) and stirred for 6–8 h (monitored by TLC).
Without isolation, 4 N HCl (6.5 mL) was added to the reaction mixture and
stirred for 4 h at 658C. After cooling, the mixture was quenched slowly
with saturated KHCO3 solution, followed by extraction with CH2Cl2
(20 ꢀ 3 mL). The combined organic layer was washed with water (the
potassium benzeneseleninate in alkaline aqueous phase could be converted
to diphenyl diselenide for reuse and dried over magnesium sulfate. Then the
solvent was removed in vacuo, and the residue was purified by flash silica-
gel column chromatography (CH2Cl2/AcOEt, 80:20–65:35) to give pure
product.
Data
5-Phenyl-oxazolidin-2-one (4a): White solid; mp. 91–928C (lit.[4b] mp. 90–
918C); 1H NMR: d ¼ 3.55 (ddd, J ¼ 0.8, 7.6, 8.6 Hz, 1H), 3.98 (ddd, J ¼ 0.8,
8.6, 8.6 Hz, 1H), 5.50 (bs, 1H, NH), 5.63 (t, J ¼ 8.6 Hz, 1H), 7.34–7.36
(m, 3H), 7.41–7.44 (m, 2H); IR (KBr): n ¼ 3278, 1721 cm21
.
5-Benzyl-oxazolidin-2-one (4b): White solid; mp. 108–1098C (lit.[4c] mp.
107–1098C); 1H NMR: d ¼ 2.94 (dd, J ¼ 6.8, 14.0 Hz, 1H), 3.15 (dd,
J ¼ 6.0, 14.0 Hz, 1H), 3.33 (ddd, J ¼ 0.8, 7.2, 8.4 Hz, 1H), 3.58 (ddd,
J ¼ 0.8, 8.4, 8.4 Hz, 1H), 4.83–4.90 (m, 1H), 5.59 (bs, 1H, NH), 7.19–7.23
(m, 3H), 7.32–7.36 (m, 2H); IR (KBr): n ¼ 3286, 1730 cm21
.
5-(Phenoxymethyl)-oxazolidin-2-one (4c): Colorless oil; 1H NMR: d ¼ 3.35
(ddd, J ¼ 0.8, 7.0, 8.5 Hz, 1H), 3.62 (ddd, J ¼ 0.8, 8.5, 8.4 Hz, 1H), 3.90 (dd,
J ¼ 9.6, 4.8 Hz, 1H), 3.95 (dd, J ¼ 9.6, 5.2 Hz, 1H), 4.83–4.90 (m, 1H), 5.45
(bs, 1H, NH), 6.96–7.01 (m, 2H), 7.26–7.29 (m, 3H); 13C NMR: d ¼ 46.4,
75.0, 76.1, 115.2, 121.7, 129.4, 135.1, 160.1; IR (KBr): n ¼ 3283,
1736 cm21; EIMS: m/z (%) ¼ 193 (Mþ). Anal. calcd. for C10H11NO3: C,
62.17; H, 5.74; N, 7.25. Found: C, 62.23; H, 5.80; N, 7.31.
5-(Benzyloxymethyl)-oxazolidin-2-one (4d): Colorless oil; 1H NMR:
d ¼ 3.33 (ddd, J ¼ 0.8, 7.0, 8.4 Hz, 1H), 3.61 (ddd, J ¼ 0.8, 8.3, 8.1 Hz,
1H), 3.89 (dd, J ¼ 4.8, 9.6 Hz, 1H), 3.93 (dd, J ¼ 5.2, 9.6 Hz, 1H), 4.56
(d, J ¼ 12.1 Hz, 1H), 4.61 (d, J ¼ 12.2 Hz, 1H), 4.85–4.89 (m, 1H), 5.53

2698
S.-R. Sheng et al.
(bs, 1H, NH), 7.02–7.08 (m, 2H), 7.31–7.35 (m, 3H); 13C NMR: d ¼ 41.7,
46.3, 75.1, 78.5, 155.6, 126.7, 128.3, 129.1, 159.5. IR (KBr): n ¼ 3286,
1738 cm21; EIMS: m/z (%) ¼ 207 (Mþ). Anal. calcd. for C11H13NO3: C,
63.76; H, 6.32; N, 6.76. Found: C, 63.79; H, 6.38; N, 6.80.
5-(4-Methylphenoxymethyl)-oxazolidin-2-one (4e): Colorless oil; 1H NMR:
d ¼ 2.31 (s, 3H), 3.34 (ddd, J ¼ 0.8, 7.1, 8.6 Hz, 1H), 3.62 (ddd, J ¼ 0.8, 8.2,
8.5 Hz, 1H), 3.90 (dd, J ¼ 5.1, 9.7 Hz, 1H), 3.95 (dd, J ¼ 5.2, 9.7 Hz, 1H),
4.85–4.93 (m, 1H), 5.52 (bs, 1H, NH), 7.52 (d, J ¼ 8.5 Hz, 2H), 6.77
(d, J ¼ 8.5 Hz, 2H); 13C NMR: d ¼ 20.4, 46.5, 76.8, 76.1, 114.5, 121.2,
129.2, 133.6, 160.2; IR (KBr): n ¼ 3284, 1740 cm21; EIMS: m/z
(%) ¼ 207 (Mþ). Anal. calcd. for C11H13NO3: C, 63.76; H, 6.32; N, 6.76.
Found: C, 63.78; H, 6.38; N, 6.81.
5-Methyloxazolidin-2-one (4f): Colorless oil (lit.[4b] oil); 1H NMR: d ¼ 1.46
(d, J ¼ 6.2 Hz, 3H), 3.21 (ddd, J ¼ 0.8, 7.2, 8.4 Hz, 1H), 3.69 (ddd, J ¼ 0.8,
8.4, 8.4 Hz, 1H), 4.74–4.82 (m, 1H), 5.57 (bs, 1H, NH); IR (neat): n ¼ 3298,
1739 cm21
.
5-Ethyl-oxazolidin-2-one (4g): White solid; mp. 51–528C (lit.[4c] mp. 51–
1
538C); H NMR: d ¼ 1.02 (t, J ¼ 7.5 Hz, 3H), 1.66–1.85 (m, 2H), 3.24
(ddd, J ¼ 1.2, 7.2, 8.4 Hz, 1H), 3.66 (ddd, J ¼ 1.2, 8.4, 8.4 Hz, 1H), 4.56–
4.62 (m, 1H), 5.32 (bs, 1H, NH); IR (KBr): n ¼ 3299, 1740 cm21
.
Cis-Cyclohexano[b]-2-oxazolidone (4h): White solid; mp. 55–568C (lit.[13]
1
mp. 558C); H NMR: d ¼ 1.15–1.46 (m, 4H), 1.60–1.84 (m, 2H), 2.10–
2.20 (m, 2H), 3.47 (ddt, J ¼ 0.8, 7.5, 8.2 Hz, 1H), 4.72–4.80 (m, 1H), 5.37
(bs, 1H, NH); IR (KBr): n ¼ 3281, 1740 cm21
.
ACKNOWLEDGMENTS
We gratefully acknowledge financial support from the National Natural
Science Foundation of China (No. 20562005) and NSF of Jiangxi Province
(No. 0620021).
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Mori, K. Eur. J. Org. Chem. 1999, 64, 2965.

Oxazolidin-2-ones
2699
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