THREE-COMPONENT REACTION OF DIMEDONE
885
9
-(4-Ethoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-
REFERENCES
tetrahydro-2H-xanthen-1,8(5H,9H)-dione (9). Yield
–
1
1
. Slobbe, P., Ruijter, E., and Orru, R.V.A., Med. Chem.
Commun., 2012, vol. 3, p. 1189. doi 10.1039/
c2md20089a
2
1
1
2
.56 g (64.8%), mp 204–206°C. IR spectrum, ν, cm :
662 (С=О). Н NMR spectrum, δ, ppm: 0.9 s and
1
.03 s (12H, CH ), 1.26 t (3H, OCH CH , J = 7.0 Hz),
3
2
3
4
5
2. Mphahlele, M.J., Gildenhuys, S., and Parbhoo, N.,
.07 d (2H, C H H , C H H , J = 16.4 Hz), 2.24 d
A
5
B
A
B
4
Molecules, 2017, vol. 5, no. 4, p. 1719. doi
(
2H, C H H , C H H , J = 16.4 Hz), 2.48 d (2H,
A B A B
1
0.4172/2161-0401.1000174
2
7
2
C H H , C H H , J = 18.6 Hz), 2.54 d (2H, C H H ,
C H H , J = 18.6 Hz), 3.93 q (2H, OCH CH , J =
A
B
A
B
A
B
3. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs),
7
A
B
2
3
Moscow: RIA “Novaya Volna,” 2012.
9
2
6
7
.0 Hz), 4.47 s (1H, C H), 6.73 d (2H, C H, C H,
Ar Ar
4. Mohamadi, M., Hassankhani, A., Ebrahimipour, S.Y.,
and Torkzadeh-Mahani, M., Int. J. Biol. Macromol.,
2017, vol. 94, Pt A, p. 85. doi 10.1016/
j.ijbiomac.2016.09.113
3
5
Ar
J = 8.8 Hz), 7.04 d (2H, C Н, C H, J = 8.8 Hz).
Ar
Found, %: С 76.31; Н 7.72. C H O . Calculated, %:
2
5
30
4
C 76.05; Н 7.61. M 394.50.
-(4-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7-
tetrahydro-2H-xanthen-1,8(5H,9H)-dione (10). Yield
5
. Antypenko, O.M., Antypenko, L.M., Kovalenko, S.I.,
Katsev, A.M., and Achkasova, O.M., Arab. J. Chem.,
9
2
016, vol. 9, no. 6, p. 792. doi 10.1016/
–
1
1
1
1
1
2
7
.7 g (45%), mp 229–231°C. IR spectrum, ν, cm :
j.arabjc.2014.09.009
1
658 (C=O). Н NMR spectrum, δ, ppm: 0.9 s and
.03 s (12Н, СH ), 2.08 d (2H, C H H , C H H , J =
6.4 Hz), 2.25 d (2H, C H H , C H H , J= 16.4 Hz),
.52 s and 2.54 s (4H, C Н , С Н ), 4.51 s (1H, C H),
6. Suresh, L., Onkara, P., Kumar, P.S.V., Pydisetty, Y.,
and Chandramouli, V.P., Bioorg. Med. Chem. Lett.,
2016, vol. 26, no. 16, p. 4007. doi 10.1016/
j.bmcl.2016.06.086
4
5
3
A
B
A
B
4
5
A
B
A
B
2
7
9
2
2
7
. Bekhit, A.A., El-Sayed, O.A., Aboulmagd, E., and
Park, J.Y., Eur. J. Med. Chem., 2004, vol. 39, p. 249.
doi 10.1016/j.ejmech.2003.12.005
.17 d and 7.25 d (4H, Ar). Found, %: C 71.96; H 6.27.
C H ClO . Calculated, %: C 71.71; H 6.49. M 384.90.
23
25
3
9
-(4-Bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-
8. Dolzhenko, A.V., Heterocycles, 2017, vol. 94, no. 10,
p. 1819. doi 10.3987/REV-17-867
9. Kour, P., Singh, V.P., Khajuria, B., Singh, T., and
Kumar, A., Tetrahedron Lett., 2017, vol. 58, p. 4179.
doi 10.1016/j.tetlet.2017.09.052
10. Zeng, L.Y. and Cai, C., J. Comb. Chem., 2010, vol. 12,
p. 35. doi 10.1021/cc9000983
11. Gein, V.L., Zamaraeva, T.M., Kazantseva, M.I.,
Gein, L.F., and Slepukhin, P.A., Russ. J. Gen. Chem.,
tetrahydro-2H-xanthen-1,8(5H,9H)-dione (11). Yield
.11 g (49.2%), mp 233–235°C. IR spectrum, ν, cm :
656 (C=O). Н NMR spectrum, δ, ppm: 0.9 s and
.05 s (12H, CH ), 2.09 s and 2.21 s (4H, C H , C H ),
.51 s and 2.53 s (4H, C H , C H ), 5.49 s (1H, C H),
.15–7.27 m (4H, Ar). Mass spectrum, m/z (I , %):
30 (100) [M + H] . Found, %: С 64.51; H 5.66.
–
1
2
1
1
2
7
4
1
4
5
3
2
2
2
7
9
2
2
rel
+
С H BrO . Calculated, %: C 64.23; H 5.82. M 429.35.
2
3
25
3
2
015, vol. 85, no. 8, p. 1984. doi 10.1134/
S1070363215080332
9
-(4-Nitrophenyl)-3,3,6,6-tetramethyl-3,4,6,7-
1
2. Odabaşoğlu, M., Kaya, M., Yıldırır, Y., and
Büyükgüngör, O., Acta Cryst. (E), 2008, vol. 64,
p. o681. doi 10.1107/S160053680800603X
tetrahydro-2H-xanthen-1,8(5H,9H)-dione (12). Yield
.91 g (48.35%), mp 221–223°C. IR spectrum, ν, cm :
662 (С=О). Н NMR spectrum, δ, ppm: 0.9 s and 1.04
s (12H, CH ), 2.09 d (2H, C H H , C H H , J =
6.0 Hz), 2.27 d (2H, C H H , C H H , J = 16.0 Hz),
.53 d (2H, C H H , C H H , J = 17.8 Hz), 2.59 d
2H, C H H , C H H , J = 17.8 Hz), 4.64 s (1H,
C H), 7.45 d (2H, C H, C H, J = 8.8 Hz), 8.08 d
–
1
1
1
1
4
5
13. Gharib, A., Fard, L.V., Pesyan, N.N., and Roshani, M.,
3
A
B
A
B
4
5
Chem. J., 2015, vol. 1, no. 3, p. 58.
1
2
(
A B A B
2
7
14. Rukovodstvo
po
provedeniyu
doklinicheskikh
A
7
B
A
B
issledovanii lekarstvennykh sredstv, (Guidelines for
Conducting Preclinical Studies of Drugs), Mironov, A.N.,
Bunyatyan, N.D., Vasil’ev, A.N., Verstakova, O.L.,
Zhuravleva, M.V., Lepakhin, V.K., Korobov, N.V.,
Merkulov, V.A., Orekhov, S.N., Sakayeva, I.V.,
Uteshev, D.B., and Yavorskii, A.N., Eds., Moscow: Grif
i K, 2012, pt 1.
2
A B A B
9
2
6
Ar
Ar
3
5
(
6
6
2H, C Н, C H, J = 8.8 Hz). Found, %: С 69.85; Н
.17; N 3.67. C H NO . Calculated, %: C 69.79; Н
23 25 5
.32; N 3.54. M 395.45.
Ar Ar
This work was performed in compliance with all
applicable international, national and institutional
guidelines for the care and use of animals.
1
1
1
5. CrysAlisPro,
Agilent
Technologies,
Version
1
.171.37.33 (release 27-03-2014 CrysAlis171 .NET).
6. Sheldrick, G.M., Acta Cryst. (A), 2008, vol. 64, p. 112.
doi 10.1107/S0108767307043930
7. Sheldrick, G.M., Acta Cryst. (C), 2015, vol. 71, p. 3. doi
10.1107/S2053273314026370
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 5 2019