1024
SOF’INA et al.
and recrystallized from dimethylformamide. Yield
1.05 g (83%). mp 229 230 C; published data [26]:
mp 226 227 C. H NMR spectrum, , ppm: CDCl3:
2. Seki, T., Sakata, H., and Iwanami, Y., J. Heterocycl.
Chem., 1995, vol. 32, no. 2, pp. 703 704.
1
3. Seki, T. and Iwanami, Y., J. Heterocycl. Chem.,
1.28 s (9H, 3CH3), 6.47 s (1H, CH), 7.12 7.30 m
(4H, Harom), 10.70 s (1H, NH); DMSO-d6): 1.22 s
(9H, 3CH3), 6.27 s (1H, CH), 7.05, 7.12, 7.28 m (4H,
Harom), 11.70 s (1H, 1-H), 13.22 s (1H, 4-H). Mass
spectrum, m/z (Irel > 5%): 244 (59) M+ , 187 (100)
[M (CH3)3C]+ (I), 160 (8), 159 (6) [M (CH3)3C
CO]+ (J), 131 (15) [M (CH3)3C 2CO]+ (K), 90 (6),
77 (7), 65 (7). The fragmentation pattern of VIa is
fully consistent with that observed for pyrido[2,3-b]-
pyrazin-2-one IIa under electron impact.
1997, vol. 34, no. 3, pp. 773 780.
4. Bodforss, S., Justus Liebigs Ann. Chem., 1964,
vol. 676, pp. 136 140.
5. Mashevskaya, I.V., Tolmacheva, I.A., and Masli-
vets, A.N., Khim. Geterotsikl. Soedin., 2000, no. 9
(399), pp. 1277 1278.
6. Mashevskaya, I.V., Tolmacheva, I.A., Kol’tso-
va, S.V., and Maslivets, A.N., Novye dostizheniya
v khimii karbonil’nykh i geterotsiklicheskikh soedi-
nenii. Sbornik nauchnykh trudov (Advances in the
Chemistry of Carbonyl and Heterocyclic Compounds.
Collection of Scientific Papers), Saratov, 2000,
p. 155.
(Z)-3-Benzoylmethylene-1H-3,4-dihydroquino-
xalin-2-one (VIb) [25 30, 35]. mp 264 265 C;
published data: mp 268 269 C [25], 266 267 C
1
[26, 29, 30], 261 263 C [35]). H NMR spectrum
7. Sof’ina, O.A., Igidov, N.M., Koz’minykh, E.N.,
Shironina, T.M., Makhova, S.E., and Koz’mi-
nykh, V.O., Abstracts of Papers, Molodezhnaya
nauchnaya shkola po organicheskoi khimii (Young
Scientists School on Organic Chemistry), Yekaterin-
burg, 1998, pp. 77 78.
(DMSO-d6), , ppm: 4.65 s (2H, CH2, tautomer F,
3%; see Scheme 3), 6.72 s (1H, CH , tautomer E,
97%, see Scheme 3; published data: 6.76 s [30],
6.80 s [35]: 100% of tautomer E), 7.20 8.15 m (5H,
Harom), 10.45 s (1H, 1-H, tautomer F), 12.05 s (1H,
1-H, tautomer E; published data: 11.85 s [30], 10.65 s
[35]), 13.68 s (1H, 4-H). According to published data
[3], no imino form F of compound VIb is detected
at 24 C in DMSO-d6, but it appears at 70 150 C,
and its fraction considerably increases as the tempera-
ture rises. 13C NMR spectrum (DMSO-d6), C, ppm:
89.9 (CHCOC6H5); 116.3 (C3); 117.4, 124.6, 124.9,
127.6, 127.8, 129.6, 132.8, 139.4, 146.5 (Carom),
156.6 (COC6H5), 189.3 (CONH).
8. Trapeznikova, N.N., Koz’minykh, E.N., Sof’i-
na, O.A., and Koz’minykh, V.O., Materialy yubilei-
noi mezhvuzovskoi nauchno-prakticheskoi konferen-
tsii 80 Let farmatsevticheskomu obrazovaniyu i
nauke na Urale: itogi i perspektivy (Proc. Jubilee
Interinstitution Scientific Practical Conf. 80 Years
of Pharmaceutical Education in the Urals: Results
and Prospects ), Perm: Permsk. Gos. Tekh. Univ.,
1998, pp. 61 62.
9. Sof’ina, O.A., Trapeznikova, N.N., Koz’mi-
nykh, E.N., Igidov, N.M., Berezina, E.S., and Koz’-
minykh, V.O., Materialy regional’noi konferentsii
Sovremennye problemy ekologii, mikrobiologii i
3-(3-Oxo-5-p-tolyl-2,3-dihydro-2-furyl)-1H-3,4-
dihydropyrido[2,3-b]pyrazin-2-one (VIII) [13]. To
a solution of 0.73 g (0.003 mol) of methyl 2-(3-oxo-5-
p-tolyl-2,3-dihydrofuran-2-ylidene)acetic acid (VII)
[15, 36] in 25 ml of ethanol we added with stirring
0.33 g (0.003 mol) of 2,3-diaminopyridine. The mix-
ture was heated for 10 min under reflux (TLC), the
solvent was removed, and the residue was ground
with 20 ml of ether and recrystallized from ethanol.
Yield 0.5 g (52%), light brown crystals with mp 220
immunologii
(Proc. Regional Conf.
Current
Problems in Ecology, Microbiology, and Immuno-
logy ), Perm: Inst. Ekol. i Genet. Mikroorg. Ural.
Otd. Ross. Akad. Nauk, 1999, pp. 105 106.
10. Sof’ina, O.A., Igidov, N.M., Koz’minykh, E.N., and
Koz’minykh, V.O., Abstracts of Papers, Nauchno-
prakticheskaya konferentsiya Farmatsevticheskaya
1
222 C (decomp.). H NMR spectrum (DMSO-d6), ,
nauka
i
praktika
(Scientific Practical Conf.
ppm: 2.33 s (3H, CH3), 3.42 br.s (3H, CHCH, 4-H),
6.55 7.90 m (8H, 4 -H, Harom, 5-H, 6-H, 7-H); the
signals were broadened and distorted because of the
poor solubility of product VIII in DMSO. Found, %:
C 67.42; H 5.11; N 12.87. C18H15N3O3. Calculated,
%: C 67.28; H 4.71; N 13.08.
Pharmaceutical Science and Practice ), Kemerovo:
Kemerovsk. Gos. Med. Akad., 1999, pp. 133 134.
11. Couturier, F., C. R. Acad. Sci., 1910, vol. 150,
no. 11, pp. 928 930; Beilstein Handbuch der orga-
nischen Chemie, EI, vol. 3, p. 264.
12. Andreichikov, Yu.S., Metody sinteza biologicheski
aktivnykh geterotsiklicheskikh soedinenii (Methods
of Synthesis of Biologically Active Heterocyclic
Compounds), Perm: Perm. Gos. Univ., 1989.
REFERENCES
1. Seki, T., Sakata, H., and Iwanami, Y., J. Heterocycl.
Chem., 1995, vol. 32, no. 1, pp. 337 338.
13. Koz’minykh, E.N., Doctoral (Chem.) Dissertation,
Perm, 1999.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 7 2001