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PANCHISHIN et al.
sion of compound IIIb in 30 ml of polyphosphoric
acid was heated at 100 C for 14 h. The reaction mix-
ture was left to stand for 12 h at 20 C, poured into
200 ml of water, stirred for 10 min, and the water was
decanted. The oily residue was dissolved in 30 ml of
ethanol, and 150 ml of water and 30 ml of saturated
sodium perchlorate were added to the solution. The
precipitate that formed was filtered off, washed with
water, dried in air, after which it was dissolved in
150 ml of boiling ethanol and left to stand for 12 h at
20 C. Compound VIb was filtered off and purified by
REFERENCES
1. Drach, B.S., Brovarets, V.S., and Smolii, O.B., Zh.
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2. Drach, B.S., Brovarets, V.S., and Smolii, O.B., Ab-
stract of Papers, Materialy 1 mezhdunarodnoi kon-
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genous Heterocycles and Alkaloids ), Moscow, 2001,
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3. Smolii, O.B., Panchishin, S.Ya., Romanenko, E.A.,
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4. Van Meervelt, L., Smolii, O.B., Mishchenko, N.I.,
Shakhnin, D.B., Romanenko, E.A., and Drach, B.S.,
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crystallization. 1H NMR spectrum (DMSO-d6),
,
3
ppm: 2.36 s (3H, CH3), 7.33 d, 7.64 d (4H, JHH
8.1 Hz, C6H4), 7.73 8.0 m (15H, 3C6H5, 2H, C7H,
3
C8H); 8.41 d, 8.44 d (2H, C6H, C9H, JHH 8.7 Hz,
3JHH 9.3 Hz), 12.00 br.s (1H, OH). The filtrate was
evaporated, and compound Vb was purified by crys-
1
tallization. H NMR spectrum (DMSO-d6), , ppm:
3
2.25 s (3H, CH3); 5.48 d (2H, CH2, JHP 15 Hz),
7.30 7.91 m (24H, 4C6H5, C6H4).
6. Smolii, O.B., Panchishin, S,Ya., Van Meervelt, L.,
Mishchenko, N.I., Romanenko, E.A., and Drach, B.S.,
Zh. Obshch. Khim., 1998, vol. 68, no. 4, p. 585.
7. Smolii, O.B., Panchishin, S.Ya., Romanenko, E.A.,
and Drach, B.S., Zh. Obshch. Khim., 1999, vol. 69,
no. 10, p. 1652.
8. Smolii, O.B., Panchishin, S.Ya., Pirozhenko, V.V.,
and Drach, B.S., Zh. Obshch. Khim., 2001, vol. 71,
no. 11, p. 1830.
2,5-Diphenyl-4-methyl-1,3-oxazole (VIIa). To a
suspension of 0.5 mmol of compound Va in 5 ml of
ethanol, a solution of 0.6 mmol of sodium methylate
in 0.15 ml of methanol was added. The reaction mix-
ture was left to stand for 12 h at 20 C, volatile com-
pounds were removed in a vacuum, and the residue
was treated with 2 ml of diethyl ether. The precipitate
was filtered off, the filtrate was evaporated, and com-
pound VIIa was purified by crystallization from
ethanol. The melting point of this sample coincides
with that of the authentic sample of 2,5-diphenyl-4-
methyl-1,3-oxazole, obtained according to [10].
9. Heterocyclic Compounds, Elderfield, R.C., Ed., New
York: Wiley, 1957, vol. 5. Translated under the title
Geterotsiklicheskie soedineniya, Moscow: Inostran-
naya Literatura, 1961, vol. 5, p. 243.
4-Methyl-5-phenyl-2- p-tolyl-1,3-oxazole
(VIIb). To a suspension of 0.5 mmol of compound
Vb in 5 ml of ethanol, a solution of 0.6 mmol of
sodium methylate in 0.15 ml of methanol was added.
The reaction mixture was left to stand for 12 h at
20 C. Compound VIIb precipitated and was filtered
off and recrystallized.
10. Lister, J. and Robinson, R., J. Chem. Soc., 1912,
vol. 101, p. 1297.
11. Naumov, V.A. and Vilkov, L.V., Molekulyarnye
struktury fosfororganicheskikh soedinenii (Molecular
Structures of Organophosphorus Compounds),
Moscow: Nauka, 1986.
12. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L.,
Orpen, A.G., and Tailor, R., J. Chem. Soc., Perkin
Trans. 2, 1987, no. 12, p. S1.
4-Triphenylphosphoranylidene-2-p-tolyl-4,5-
dihydronaphtho[2,1-d][1.3]oxazol-5-one (VIII). To
a suspension of 0.4 mmol of compound VIb in 5 ml
of absolute methanol, 0.45 mmol of sodium methylate
in 12 ml of methanol was added. The reaction mixture
was stirred for 2 h at 40 C. Compound VIII preci-
pitated and was filtered off, washed with water, and
recrystallized.
13. Sheldric, G.M., SHELXS-86. Program for the Solution
of Crystal Structures, Goettingen: Univ. of Goettin-
gen, 1986.
14. Sheldric, G.M., SHELXS-93. Program for the Refi-
nement of Crystal Structures, Goettingen: Univ. of
Goettingen, 1993.
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