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LIPUNOVA et al.
2,4-Difluoro-3-NR1R2-6a,10a-dihydro-8-R-9-R-
REFERENCES
12H-benzo[e]benzo[4,5]imidazo[2,1-b]-[1,3]thiazin-
12-ones (XII). (a) To 0.7 g (2.3 mmol) of compound
IIIa in 7 ml of anhydrous pyridine was added 0.7 ml
(9.2 mmol) of pyrrolidine. The reaction mixture was
heated to boiling for 5 h, and on cooling the separated
precipitate of compound XIIa was filtered off and
recrystallized from DMSO. Yield 0.8 g (91%). In the
same way was prepared compound XIIe.
1. Lipunova, G.N., Nosova, E.V., Sidorova, L.P.,
Charushin, V.N., Chasovskikh, O.M., and Tka-
chev, A.V., Zh. Org. Khim., 2002, vol. 38, p. 1851.
2. Lipunova, G.N., Mokrushina, G.A., Nosova, E.V.,
Rusinova, L.I.,
and Charushin, V.N., Mend.
Communn., 1997, no. 3, p. 109.
3. Kotovskaya, S.K., Perova, N.M., Baskakova, Z.M.,
Romanova, S.A., Charushin, V.N., and Chupa-
khin, O.N., Zh. Org. Khim., 2001, vol. 37, p. 598.
4. Mokrushina, G.A., Nosova, E.V., Lipunova, G.N.,
and Charushin, V.N., Zh. Org. Khim., 1999, vol. 35,
p. 1447.
5. Charushin, V.N., Lipunova, G.N., Nosova, E.V.,
Sidorova, L.P., and Chasovskikch, O.M., Mendeleev
Communn., 1998, no. 4, p. 131.
(b) To 0.5 g (1.6 mmol) of compound IIIa in 7 ml
of anhydrous dimethylformamide was added 0.9 g
(6.4 mmol) 3-(4-morpholino)-1-propanamine. The re-
action mixture was boiled for 5 h, then cooled. The
separated precipitate of compound XIIc was filtered
off and recrystallized from DMSO. Yield 0.45 g
(65%). Similarly were prepared compounds
XIIb, d, f. Yields, melting points, and elemental
analyses of compounds XII are given in Table 6.
6. Lipunova, G.N., Nosova, E.V., Mokrushina, G.A.,
Sidorova, L.P., and Charushin, V.N., Khim.-Farm.
Zh., 2000, p. 20.
1-NR1R2-2, 4-Difluoro-3-NR1R2-6a, 10a-
dihydro-8-R-9-R-12H-benzo[e]benzo[4,5]imidazo-
7. Lipunova, G.N., Nosova, E.V., Mochul,skaya, N.N.,
Andreiko, A.A., Chasovskikh, O.M., and Charu-
shin, V.N., Izv., Akad. Nauk, Ser. Khim.
[2,1-b][1,3]thiazin-12-ones (XIII). To 0.7
g
(2.1 mmol) of compound IIIb in 5 ml of anhydrous
dimethylformamide was added 1.4 ml (10.2 mmol)
of 3-(4-morpholino)-1-propanamine. The reaction mix-
ture was boiled for 5 h, then cooled. The separated
precipitate of compound XIIIa was filtered off and
recrystallized from DMSO. Yield 0.8 g (67%).
Similarly were prepared compounds XIIIb h.
19F NMR spectrum of compound XIIIc (DMSO-d6),
8. Shen, L.L., Quinolone Antibacterial Agents,
Washington: American Society for Microbiology,
1993, p. 77.
9. Furin, G.G., Ftorsoderzhashchie geterotsiklicheskie
soedineniya: sintez i primenenie (Fluorocontaining
Heterocyclic Compounds: Synthesis and Application),
Novosibirsk: Nauka, 2001, 304 p.
10. Granik, V.G., Osnovy meditsinskoi khimii, Moscow:
Vuzovskaya kniga, 2001.
11. Giannola, L.I., Bajardi, M.L., and Palazzo, S., J. Het.
Chem., 1977, vol. 14, p. 507.
12. Nageswar, Y.V.D., Murty, M.S.R., and Ramalin-
gam, T., Indian J. Chem., 1988, vol. 27B, p. 1142.
13. Rao, K.V.B., Charles, E.S., and Sharma, S., Indian
J. Chem., 1981, vol. 20B, p. 575.
14. George, T. and Tahilramani, R., J. Org. Chem.,
1971, vol. 36, p. 2190.
15. Dolbier, W.R., Burkholder, C., Abboud, K.A., and
Loehle, D., J. Org. Chem., 1994, vol. 59, p. 7688.
16. Nosova, E.V., Lipunova, G.N., Sidorova, L.P., and
Charushin, V.N., Zh. Org. Khim., 2001, vol. 37,
p. 1228.
4
F, ppm: 129.12 d (1F, JFF 6.4), 127.11 d (1F,
4JFF 6.4). Yields, melting points, and elemental
analyses of compounds XIII are given in Table 6.
7,9-Difluoro-8-NR1R2-2,3-dihydro-5H-benzo-
[4,5]imidazo[2,1-b][1,3]thiazin-5-ones (XIV). To
0.6 g (2.3 mmol) of compound VIII in 7 ml of
anhydrous dimethylformamide was added 0.7 ml
(8.2 mmol) of pyrrolidine. The reaction mixture was
boiled for 4 h, then cooled and diluted with water
(25 ml). The separated precipitate was filtered off and
recrystallized from ethanol Yield 0.7 g (97%). Com-
pounds XIVb e were obtained in the similar way.
Yields, melting points, and elemental analyses of
compounds XIV are given in Table 6.
The study was carried out under financial support
of Russian Foundation for Basic Research (grant
no. 00-03032785a), Russian Foundation for Basic
Research-Ural (grant no. 101-03-96427), and also of
American Civil Research and Development Founda-
tion (CRDF) (grant no. REC-005).
17. Moran, D.B., Ziegler, C.B., Dunne, T.S.,
Kuck, N.A., and Lin, Y., J. Med. Chem., 1989,
vol. 32, p. 1313.
18. Vereshchagina, N.N., Postovskii, I.Ya., and Bed-
nyagina, N.P., Khim. Geterotsikl. Soed., 1967, ch. 1,
p. 162.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 2 2003