New syntheses on the basis of 4-hydroxy-2H-chromen-2-ones

Article abstract of DOI:10.1134/S1070428009070161

Alkylation of 4-hydroxy-2H-chromen-2-ones with 2-chloromethyloxirane in acetone in the presence of potassium carbonate gave 4-(2,3-epoxypropoxy)-2H- chromen-2-ones which were treated with various amines to obtain the corresponding 4-(3-amino-2-hydroxyprop

Full text of DOI:10.1134/S1070428009070161

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 7, pp. 1086–1090. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © A.A. Avetisyan, A.G. Alvandzhyan, K.S. Avetisyan, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 7,
pp. 1098–1101.
New Syntheses on the Basis of 4-Hydroxy-2H-chromen-2-ones
A. A. Avetisyan, A. G. Alvandzhyan, and K. S. Avetisyan
Erevan State University, ul. A.Manukyana 1, Erevan, 375025 Armenia
e-mail: organkim@sun.ysu.am
Received January 25, 2008
Abstract—Alkylation of 4-hydroxy-2H-chromen-2-ones with 2-chloromethyloxirane in acetone in the pres-
ence of potassium carbonate gave 4-(2,3-epoxypropoxy)-2H-chromen-2-ones which were treated with various
amines to obtain the corresponding 4-(3-amino-2-hydroxypropoxy)-2H-chromen-2-ones, and the latter were
acylated at the hydroxy group with benzoyl chloride.
DOI: 10.1134/S1070428009070161
In continuation of our studies in the field of syn-
thesis of new O-alkyl derivatives of chromenes [1], in
the present work we performed alkylation of 4-hy-
droxy-2H-chromen-2-ones Ia–Ie with 2-chloromethyl-
oxirane. Effects of various factors on the process were
studied, and optimal reaction conditions were devel-
oped. 4-(2,3-Epoxypropoxy)-2H-chromen-2-ones IIa–
IIe were synthesized by heating compounds Ia–Ie with
chloromethyloxirane at a ratio of 1:1.5 in anhydrous
acetone in the presence of potassium carbonate
(Scheme 1). The product structure was confirmed by
elemental analyses and IR and NMR spectra.
It is known that reactions of epoxy derivatives with
amines underlie convenient procedures for the prepara-
tion of amino alcohols which are used as intermediate
products in syntheses of natural and biologically active
organic compounds [2–8]. Various vicinal amino alco-
hols and their derivatives functionalized at the hydroxy
Scheme 1.
HO
O
R4
N
R3
R1
OH
O
R1
O
R1
O
R2
O
R2
O
R2
O
K2CO3. Me2CO
R3R4NH, dioxane
Cl
+
O
O
O
Ia–Ie
IIa–IIe
IIIa–IIIe, IVa–IVe, Va–Ve, VIa–VIe
VIIa–VIIe, VIIIa–VIIIe
R1 = R2 = H (a); R1 = Me, R2 = H (b); R1 = H, R2 = i-Bu (c), Me (d), Pr (e); III, R3 = H, R4 = PhCH2; IV, R3R4N = morpholino;
V, R3R4N = pyrrolidin-1-yl; VI, R3R4N = piperidino; VII, R3 = H, R4 = 4-MeOC6H4; VIII, R3 = H, R4 = naphthalen-1-yl.
Scheme 2.
O
O
O
R4
O
O
O
R4
N
N
Ph
R3
Ph
R3
NH3
PhCOCl
IVa–VIa
· HCl
O
O
O
O
IXa–IXc
Xa–Xc
IX, X, R3R4N = morpholino (a), pyrrolidin-1-yl (b), piperidino (c).
1086

NEW SYNTHESES ON THE BASIS OF 4-HYDROXY-2H-CHROMEN-2-ONES
1087
group exhibit biological activity or are used as medi-
cines [9, 10]. It is also known [11–13] that opening of
the oxirane ring by the action of nucleophiles follows
Krasuskii rule provided that electronegative substituent
(–I) is present at the oxirane ring.
4-(2,3-Epoxypropoxy)-3-isobutyl-2H-chromen-2-
one (IIc). Yield 4.1 g (74%), mp 172°C. IR spectrum,
ν, cm–1: 1720 (C=O), 1615 (C=Carom), 1250, 1010, 835
(oxirane). Found, %: C 71.05; H 6.75. C16H18O4. Cal-
culated, %: C 70.73; H 6.57.
With a view to obtain new β-amino alcohol
derivatives as potential biologically active substances,
4-(2,3-epoxypropoxy)-2H-chromen-2-ones IIa–IIe
were brought into reaction with benzylamine, 1-naph-
thylamine, p-anisidine, piperidine, pyrrolidine, and
morpholine. The optimal reaction conditions were as
follows: reactant molar ratio (II–amine) 1:1.5, solvent
dioxane, temperature 85–90°C, reaction time 6 h. The
products were the corresponding amino alcohols III–
VIII (Scheme 1) whose structure was confirmed by
elemental analyses and spectral data. Amino alcohols
IVa–VIa were treated with benzoyl chloride, and ben-
zoate hydrochlorides IXa–IXc thus formed were con-
verted into free bases Xa–Xc by the action of aqueous
ammonia (Scheme 2).
4-(2,3-Epoxypropoxy)-3-methyl-2H-chromen-2-
one (IId). Yield 3.32 g (72%), mp 169°C. IR spectrum,
ν, cm–1: 1720 (C=O), 1620 (C=C), 1250, 1010, 840
(oxirane). Found, %: C 67.32; H 6.41. C13H12O4. Cal-
culated, %: C 67.24; H 6.57.
4-(2,3-Epoxypropoxy)-3-propyl-2H-chromen-2-
one (IIe). Yield 3.66 g (71%), mp 164°C. Found, %:
C 68.97; H 6.05. C15H16O4. Calculated, %: C 69.23;
H 6.15.
4-(3-Benzylamino-2-hydroxypropoxy)-2H-chro-
men-2-one (IIIa). A mixture of 2.18 g (10 mmol) of
compound IIa, 1.16 (10 mmol) of freshly distilled
benzylamine, and 10 ml of dioxane was heated for 6 h
at 89–90°C. The solvent was removed under reduced
pressure, and the residue was washed with hexane and
recrystallized from chloroform–petroleum ether (1:1).
Yield 2.6 g (80%), mp 183°C. IR spectrum, ν, cm–1:
3520 (NH), 3240 (OH), 1720 (C=O), 1610 (C=C),
EXPERIMENTAL
The IR spectra were recorded on a UR-20 spectro-
photometer from samples dispersed in mineral oil. The
1H NMR spectra were measured on a Tesla BS-497
instrument (100 MHz) from solutions in CDCl3 using
hexamethyldisiloxane as internal reference.
1
1245 (C–O–C). H NMR spectrum, δ, ppm: 7.60–
8.05 m (4H, Harom), 7.20 (3H, Harom, J = 7.2 Hz),
6.95 (2H, Harom, J = 8.5 Hz), 5.80 (1H, CH), 4.30 m
(CHOH), 3.95 d (1H, OCH2, J = 4.5 Hz), 3.80 d (2H,
CH2Ph, J = 12.8 Hz), 3.75 d (1H, OCH2, J = 3.5 Hz),
3.50 m (2H, NH, OH), 2.75 d.d (1H, CH2N, J = 7.5,
12.8 Hz), 2.60 d.d (1H, CH2N, J = 7.5, 12.8 Hz).
Found, %: C 70.25; H 5.62; N 4.25. C19H19NO4. Cal-
culated, %: C 70.15; H 5.85; N 4.31.
4-(2,3-Epoxypropoxy)-2H-chromen-2-one (IIa).
A mixture of 3.24 g (20 mmol) of 4-hydroxy-2H-
chromen-2-one (Ia), 28 g (20 mmol) of potassium
carbonate, and 1.9 ml (30 mmol) of 2-chloromethyl-
oxirane in 3 ml of acetone was heated for 5 h at 70°C.
The mixture was cooled, diluted with water, and ex-
tracted with diethyl ether. The extract was evaporated,
and the residue was recrystallized from aqueous al-
cohol (1 :1). Yield 3.4 g (78%), colorless crystals,
mp 162°C. IR spectrum, ν, cm–1: 1725 (C=O), 1610,
1565, 1525 (C=Carom), 1250, 1020, 840 (oxirane).
1H NMR spectrum, δ, ppm: 6.8–7.0 m (4H, Harom),
5.8 s (1H, CH), 2.95 m (1H, CH), 2.35–2.65 m (4H,
CH2). Found, %: C 65.75; H 4.61. C12H10O4. Calculat-
ed, %: C 66.00; H 4.59.
Compounds IIIb–IIIe, IVa–IVe, Va–Ve, VIa–VIe,
VIIa–VIIe, and VIIIa–VIIIe were synthesized in
a similar way.
4-(3-Benzylamino-2-hydroxypropoxy)-5-methyl-
2H-chromen-2-one (IIIb). Yield 2.64 g (78%),
mp 185–186°C (from CHCl3). IR spectrum, ν, cm–1:
3420 (NH), 3240 (OH), 1720 (C=O), 1610 (C=C),
1260. Found, %: C 71.05; H 6.21; N 4.21. C20H21NO4.
Calculated, %: C 70.796; H 6.195; N 4.130.
4-(3-Benzylamino-2-hydroxypropoxy)-3-iso-
butyl-2H-chromen-2-one (IIIc). Yield 2.8 g (75%),
mp 173–174°C (from CHCl3). Found, %: C 71.95;
H 7.13; N 3.71. C23H27NO4. Calculated, %: C 72.44;
H 7.09; N 3.675.
Compounds IIb–IIe were synthesized in a similar
way.
4-(2,3-Epoxypropoxy)-5-methyl-2H-chromen-2-
one (IIb). Yield 3.53 g (76%), mp 174°C. IR spectrum,
ν, cm–1: 1725 (C=O), 1620 (C=C), 1250, 1015, 840
(oxirane). Found, %: C 67.52; H 5.21. C13H12O4. Cal-
culated, %: C 67.24; H 6.57.
4-(3-Benzylamino-2-hydroxypropoxy)-3-methyl-
2H-chromen-2-one (IIId). Yield 2.65 g (79%),
mp 189–190°C (from CHCl3). Found, %: C 70.87;
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AVETISYAN et al.
1088
H 6.05; N 4.23. C20H21NO4. Calculated, %: C 70.96;
H 6.19; N 4.13.
4-[2-Hydroxy-3-(pyrrolidin-1-yl)propoxy]-5-
methyl-2H-chromen-2-one (Vb). Yield 2 g (68%),
mp 169°C (from CCl4–petroleum ether, 2:1). Found,
%: C 67.52; H 7.01; N 4.58. C17H21NO4. Calculated,
%: C 67.33; H 6.93; N 4.62.
4-(3-Benzylamino-2-hydroxypropoxy)-3-propyl-
2H-chromen-2-one (IIIe). Yield 2.7 g (74%),
mp 166–167°C (from CHCl3). Found, %: C 71.81;
H 6.73; N 3.49. C22H25NO4. Calculated, %: C 71.94;
H 6.81; N 3.82.
4-[2-Hydroxy-3-(pyrrolidin-1-yl)propoxy]-3-iso-
butyl-2H-chromen-2-one (Vc). Yield 2.3 g (65%),
mp 192–193°C (from CCl4–petroleum ether, 2:1).
Found, %: C 69.32; H 7.64; N 4.17. C20H27NO4. Cal-
culated, %: C 69.57; H 7.83; N 4.06.
4-(2-Hydroxy-3-morpholinopropoxy)-2H-chro-
men-2-one (IVa). Yield 2.35 g (77%), mp 191°C
(from CHCl3–petroleum ether, 1:1). IR spectrum, ν,
cm–1: 3245 (OH), 1720 (C=O), 1620, 1560, 1525
4-[2-Hydroxy-3-(pyrrolidin-1-yl)propoxy]-3-
methyl-2H-chromen-2-one (Vd). Yield 1.87 g (64%),
mp 136–137°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 67.15; H 6.87; N 4.70. C17H21NO4. Cal-
culated, %: C 67.33; H 6.93; N 4.62.
1
(C=Carom), 1240 (COC). H NMR spectrum, δ, ppm:
7.40–8.15 m (4H, Harom), 5.70 s (1H, CH), 4.80 br.s
(1H, OH), 4.10 m (2H, OCH2, CHOH), 4.00 m (1H,
OCH2, J = 3.5 Hz), 3.60 m (4H, CH2OCH2), 2.65 d
(2H, NCH2, J = 7.6 Hz), 2.28 m (4H, CH2NCH2).
Found, %: C 62.4; H 6.50; N 4.25. C16H19NO5. Cal-
culated, %: C 62.95; H 6.23; N 4.59.
4-[2-Hydroxy-3-(pyrrolidin-1-yl)propoxy]-3-
propyl-2H-chromen-2-one (Ve). Yield 2.13 g (65%),
mp 129–130°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 69.10; H 7.73; N 4.35. C19H25NO4. Cal-
culated, %: C 68.88; H 7.55; N 4.23.
4-(2-Hydroxy-3-morpholinopropoxy)-5-methyl-
2H-chromen-2-one (IVb). Yield 2.47 g (74%),
mp 187–188°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 63.3; H 6.25; N 4.16. C17H21NO5. Cal-
culated, %: C 63.95; H 6.58; N 4.39.
4-(2-Hydroxy-3-piperidinopropoxy)-2H-chro-
men-2-one (VIa). Yield 2.24 g (74%), mp 167°C
(from CHCl3–petroleum ether, 1:1). IR spectrum, ν,
cm–1: 3260 (OH), 1720 (C=O), 1620, 1560, 1520
4-(2-Hydroxy-3-morpholinopropoxy)-3-isobutyl-
2H-chromen-2-one (IVc). Yield 2.62 g (73%),
mp 179–180°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 67.10; H 7.25; N 3.67. C20H27NO5. Cal-
culated, %: C 66.48; H 7.48; N 3.88.
1
(C=Carom), 1240 (COC). H NMR spectrum, δ, ppm:
7.70–8.10 m (4H, Harom), 5.82 s (1H, CH), 4.85 br.s
(1H, OH), 4.25 m (2H, OCH2, CHOH), 3.80 d (1H,
OCH2, J = 3.5 Hz), 2.6 d.d (1H, NCH2, J = 8.2,
12.7 Hz), 2.4 d.d (1H, NCH2, J = 8.2, 12.7 Hz), 2.15 m
(4H, CH2NCH2), 1.32 m (6H, CH2). Found, %:
C 67.25; H 7.02; N 4.58. C17H21NO4. Calculated, %:
C 67.33; H 6.93; N 4.62.
4-(2-Hydroxy-3-morpholinopropoxy)-3-methyl-
2H-chromen-2-one (IVd). Yield 2.41 g (76%),
mp 157–158°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 63.15; H 6.22; N 4.31. C17H21NO5. Cal-
culated, %: C 63.95; H 6.58; N 4.39.
4-(2-Hydroxy-3-piperidinopropoxy)-5-methyl-
2H-chromen-2-one (VIb). Yield 2.28 g (72%),
mp 176°C (from CHCl3–petroleum ether, 1:1). Found,
%: C 68.27; H 7.14; N 4.51. C18H23NO4. Calculated,
%: C 68.14; H 7.26; N 4.42.
4-(2-Hydroxy-3-morpholinopropoxy)-3-propyl-
2H-chromen-2-one (IVe). Yield 2.47 g (71%),
mp 144–145°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 65.47; H 7.31; N 4.17. C19H25NO5. Cal-
culated, %: C 65.71; H 7.20; N 4.035.
4-(2-Hydroxy-3-piperidinopropoxy)-3-isobutyl-
2H-chromen-2-one (VIc). Yield 2.3 g (64%),
mp 182°C (from CHCl3–petroleum ether, 1:1). Found,
%: C 70.22; H 8.10; N 3.71. C21H29NO4. Calculated,
%: C 70.19; H 8.08; N 3.89.
4-[2-Hydroxy-3-(pyrrolidin-1-yl)propoxy]-2H-
chromen-2-one (Va). Yield 2.1 g (71%), mp 175°C
(from CCl4–petroleum ether, 2:1). IR spectrum, ν,
cm–1: 3260 (OH), 1720 (C=O), 1620, 1565, 1520
1
4-(2-Hydroxy-3-piperidinopropoxy)-3-methyl-
2H-chromen-2-one (VId). Yield 2.2 g (70%),
mp 174–175°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 68.14; H 7.26; N 4.51. C18H23NO4. Cal-
culated, %: C 68.14; H 7.26; N 4.42.
(C=Carom), 1250 (COC). H NMR spectrum, δ, ppm:
7.6–7.9 m (4H, Harom), 5.75 s (1H, CH), 4.80 br.s (1H,
OH), 4.20 m (2H, OCH2, CHOH), 3.68 d (1H, OCH2,
J = 3.6 Hz), 2.54 m (4H, CH2CH2), 2.42 d.d (1H,
NCH2, J = 7.7, 12.6 Hz), 1.82 m (4H, CH2NCH2).
Found, %: C 66.20; H 6.45; N 4.25. C16H19NO4. Cal-
culated, %: C 66.44; H 6.57; N 4.84.
4-(2-Hydroxy-3-piperidinopropoxy)-3-propyl-
2H-chromen-2-one (VIe). Yield 2.17 g (63%),
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NEW SYNTHESES ON THE BASIS OF 4-HYDROXY-2H-CHROMEN-2-ONES
1089
mp 167–168°C (from CHCl3–petroleum ether, 1:1).
Found, %: C 69.63; H 7.49; N 4.11. C20H27NO4. Cal-
culated, %: C 69.56; H 7.89; N 4.06.
H 6.59; N 3.45. C26H27NO4. Calculated, %: C 74.82;
H 6.47; N 3.36.
4-[2-Hydroxy-3-(naphthalen-1-ylamino)pro-
poxy]-3-methyl-2H-chromen-2-one (VIIId). Yield
3.1 g (82%), mp 225–226°C. Found, %: C 73.45;
H 5.32; N 43.81. C23H21O4N. Calculated, %: C 73.60;
H 5.60; N 3.73.
4-[2-Hydroxy-3-(4-methoxyphenylamino)pro-
poxy]-2H-chromen-2-one (VIIa). Yield 2.18 g (67%),
mp 187–188°C. IR spectrum, ν, cm–1: 3520 (NH),
3445 (OH), 3030 (C–Harom), 1720 (C=O), 1610
(C=Carom), 1580 (δ NH), 1250 (COC). Found, %:
C 70.34; H 5.67; N 4.25. C19H19NO5. Calculated, %:
C 66.86; H 5.57; N 4.11.
4-[2-Hydroxy-3-(naphthalen-1-ylamino)pro-
poxy]-3-propyl-2H-chromen-2-one (VIIIe). Yield
3.6 g (84%), mp 210–211°C. Found, %: C 74.64;
H 6.38; N 3.64. C25H25O4N. Calculated, %: C 74.44;
H 6.20; N 3.47.
4-[2-Hydroxy-3-(4-methoxyphenylamino)pro-
poxy]-5-methyl-2H-chromen-2-one (VIIb). Yield
2.25 g (67%), mp 201–202°C. Found, %: C 67.50;
H 5.31; N 3.52. C20H21NO5. Calculated, %: C 67.61;
H 5.92; N 3.94.
4-[2-Benzoyloxy-3-(2-oxo-2H-chromen-4-yloxy)-
propyl]morpholin-4-ium chloride (IXa). A mixture
of 4 g (13 mmol) of compound IVa and 1.83 g
(13 mmol) of benzoyl chloride in 5 ml of toluene was
kept for 15–20 h at room temperature and was then
heated for 3 h at 90–95°C. The mixture was cooled,
and the precipitate was filtered off, washed with
diethyl ether, and dried. Yield 5.45 g (93%), mp 289–
291°C. Found, %: C 62.05; H 5.27; Cl 7.79; N 3.21.
C23H23NO6 ·HCl. Calculated, %: C 61.95; H 5.39;
Cl 7.97; N 3.14.
4-[2-Hydroxy-3-(4-methoxyphenylamino)pro-
poxy]-3-isobutyl-2H-chromen-2-one (VIIc). Yield
2.61 g (69%), mp 197–198°C. Found, %: C 69.56;
H 6.98; N 3.61. C23H27NO5. Calculated, %: C 69.52;
H 6.80; N 3.53.
4-[2-Hydroxy-3-(4-methoxyphenylamino)pro-
poxy]-3-methyl-2H-chromen-2-one (VIId). Yield
2.19 g (65%), mp 204–205°C. Found, %: C 67.86;
H 5.75; N 3.47. C20H21NO5. Calculated, %: C 67.61;
H 5.92; N 3.94.
Compounds IXb and IXc were synthesized in
a similar way.
4-[2-Hydroxy-3-(4-methoxyphenylamino)pro-
poxy]-3-propyl-2H-chromen-2-one (VIIe). Yield
2.39 g (65%), mp 183–184°C. Found, %: C 68.60;
H 7.05; N 3.75. C22H25NO5. Calculated, %: C 68.93;
H 6.53; N 3.66.
1-[2-Benzoyloxy-3-(2-oxo-2H-chromen-4-yloxy)-
propyl]pyrrolidinium chloride (IXb). Yield 5.16 g
(93%), mp 285–287°C. Found, %: C 64.31; H 5.48;
Cl 8.39; N 3.17. C23H23NO5 ·HCl. Calculated, %:
C 64.26; H 5.36; Cl 8.27; N 3.26.
4-[2-Hydroxy-3-(naphthalen-1-ylamino)pro-
poxy]-2H-chromen-2-one (VIIIa). Yield 2.92 g
(81%), mp 213–214°C (from CHCl3–petroleum ether,
1:1). IR spectrum, ν, cm–1: 3460 (OH), 3230 (NH),
3030 (C–Harom), 1720 (C=O), 1620 (C=Carom), 1610
1-[2-Benzoyloxy-3-(2-oxo-2H-chromen-4-yloxy)-
propyl]piperidinium chloride (IXc). Yield 5.45 g
(95%), mp 297–299°C. Found, %: C 65.01; H 5.78;
Cl 7.96; N 3.22. C24H25NO5 ·HCl. Calculated, %:
C 64.94; H 5.86; Cl 8.00; N 3.16.
1
(C=Carom), 1580 (δNH), 1245 (COC). H NMR spec-
2-Morpholino-1-[(2-oxo-2H-chromen-4-yloxy)-
methyl]ethyl benzoate (Xa). A suspension of com-
pound IXa in 3 ml of benzene was treated with an am-
monia solution to attain pΗ 10. The precipitate was
filtered off, dried, and recrystallized from chloroform–
petroleum ether (1:1). Yield 3.37 g (83%), mp 212–
213°C. IR spectrum, ν, cm–1: 3035 (C–Harom), 1745
(C=O, ester), 1720 (C=O, lactone), 1620, 1560, 1530
trum, δ, ppm: 2.85 t (2H, NCH2, J = 7.5 Hz), 4.25 d
(1H, OCH2, J = 5.7 Hz), 4.35 m (1H, CHOH), 4.85 d
(1H, OH), 7.3–8.05 m (10H, Harom), 7.20 d (1H, Harom),
7.00 d (1H, Harom). Found, %: C 73.26; H 5.32; N 4.05.
C22H19NO4. Calculated, %: C 73.13; H 5.26; N 3.88.
4-[2-Hydroxy-3-(naphthalen-1-ylamino)pro-
poxy]-5-methyl-2H-chromen-2-one (VIIIb). Yield
3.1 g (82%), mp 222–223°C. Found, %: C 73.25;
H 5.71; N 3.84. C23H21NO4. Calculated, %: C 73.60;
H 5.60; N 3.73.
1
(C=Carom), 1245 (COC). H NMR spectrum, δ, ppm:
7.30–7.52 m (5H, Harom), 6.90–7.20 m (4H, Harom),
5.9 s (1H, CH), 3.90 m (3H, CH2O, CHO), 3.60 m
(4H, CH2OCH2), 2.68 m (6H, CH2N). Found, %:
C 67.53; H 5.69; N 3.22. C23H23NO6. Calculated, %:
C 67.48; H 5.62; N 3.42.
4-[2-Hydroxy-3-(naphthalen-1-ylamino)pro-
poxy]-3-isobutyl-2H-chromen-2-one (VIIIc). Yield
3.48 g (84%), mp 207–208°C. Found, %: C 75.00;
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AVETISYAN et al.
1090
3. Karpf, M. and Trussardi, R.J., J. Org. Chem., 2001,
vol. 66, p. 2044.
4. Inaba, T., Yamada, Y., Abe, H., Sagawa, S., and Cho, H.,
Compounds Xb and Xc were synthesized in
a similar way.
1-[(2-Oxo-2H-chromen-4-yloxy)methyl]-2-(pyr-
rolidin-1-yl)ethyl benzoate (Xb). Yield 3.3 g (84%),
mp 201–202°C. IR spectrum, ν, cm–1: 3030 (C–Harom),
1740 (C=O, ester), 1720 (C=O, lactone), 1625, 1560,
1525 (C=Carom), 1250 (COC). Found, %: C 70.41;
H 5.69; N 3.43. C23H23NO5. Calculated, %: C 70.23;
H 5.85; N 3.56.
J. Org. Chem., 2000, vol. 65, p. 1623.
5. Cristau, H.J., Pirat, J.L., Drag, M., and Kafarski, P.,
Tetrahedron Lett., 2000, vol. 41, p. 9781.
6. Hudlicky, T., Abbod, K.F., Entwisle, D.A., Fan, R.,
Maurya, R., Thorpe, A.J., Bolonick, J., and Myers, B.,
Synthesis, 1996, no. 7, p. 897.
7. FRG Patent Appl. no. 19724186, 1998; Ref. Zh., Khim.,
2002, no. 19O116P.
8. Sabitha, G., Babu, R.S., Rajkumar, M., and Yadav, J.S.,
1-[(2-Oxo-2H-chromen-4-yloxy)methyl]-2-piper-
idinoethyl benzoate (Xc). Yield 3.47 g (85%),
mp 185–186°C. H NMR spectrum, δ, ppm: 7.50–
7.30 m (5H, Harom), 6.97–7.10 m (4H, Harom), 5.82 s
(1H, CH), 3.85 m (3H, CH2O, CHO), 2.30 m (6H,
CH2N), 1.50 m (4H, CH2), 1.40 m (2H, CH2). Found,
%: C 70.43; H 6.27; N 3.61. C24H25NO5. Calculated,
%: C 70.76; H 6.14; N 3.44.
Org. Lett., 2002, vol. 4, p. 343.
1
9. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs),
Moscow: Novaya Volna, 2002, vol. 1, pp. 253, 368,
385; vol. 2, pp. 295, 303, 362.
10. Lukevits, E.Ya., Libert, L.I., and Voronkov, M.G., Usp.
Khim., 1970, vol. 39, p. 2005.
11. Mislyuk, O.A., Shibaev, V.I., Davidenkov, L.R.,
Vyunov, K.A., and Ginak, A.I., Zh. Prikl. Khim., 1984,
vol. 57, p. 2138.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 7 2009