SYNTHESIS AND CYCLIZATION OF DIKETONES
259
for 24 h. Then 20 ml of 10% HCl was added, and the
mixture was boiled for 6 h. The chloroform layer was
separated, washed with 10% solution of Na2CO3,
then with water, dried, the chloroform was distilled
off, and the dry residue was recrystallized first from
hexane and then from 50% aqueous ethanol.
vol. 30, no. 11, pp. 3711 3714.
9. Mitsuhashi, Kemmotsu, Nomura, Keiichi, Watana-
be, Isao, and Minami, Norio, Chem. Pharm. Bull.,
1969, vol. 17, no. 8, pp. 1572 1577.
10. Zhang, Pang and Li, Lian-chu, Synth. Commun.,
1986, vol. 16, no. 8, pp. 957 965.
11. Kirrmann, A. and Warselman, C., Bull. Soc. Chim.,
1967, no. 10, pp. 3766 3772.
2-(1-Adamantanoylmethyl)cyclopentan-1-one
(VII) and 2-(1-adamantanoylmethyl)cyclohexan-1-
one (VIII). A solution of 1 g (3.9 mmol) of halo-
ketone VI and 4.3 mmol of enamine in 10 ml of
anhydrous benzene was refluxed for 4 h. Then 10 ml
of 10% HCl was added, and the mixture was refluxed
for 12 h more. The benzene layer was separated,
washed with water, dried on calcium chloride, the
benzene was distilled off, and the residue was re-
crystallized from hexane.
12. Solomoichenko, T.N., Kozhemyakina, I.M., Za-
slavskii, V.G., Minkina, L.V., and Savelova, V.A.,
Ukr. Khim. Zh., 1990, vol. 56, no. 8, pp. 867 871.
13. Hunig, S. and Hoch, H., Tetrahedron Lett., 1966,
no. 42, pp. 5215 5220.
14. Opitz, G. and Tempel, E., Lieb. Ann., 1966, vol. 699,
no. 1, pp. 74 87.
15. Jacquier, R. and Petrus, F., Bull. Soc. Chim., 1970,
no. 7, pp. 2599 2636.
16. Grudwell, E., Pinnegar, M.A., and Templeton, W.,
J. Med. Chem., 1965, vol. 8, no. 1, pp. 41 45.
17. Hunig, S., Buysch, H.J., and Hoch, H., Chem. Ber.,
1967, vol. 100, no. 12, pp. 3996 4009.
18. Hunig, S. and Buysch, H.J., Chem. Ber., 1967,
vol. 100, no. 12, pp. 4010 4016.
3-(1-Adamantyl)-5,6-dihydro-4H-cyclopenta[c]-
isoxazole (IX). To a solution of 1 g (4,1 mmol) of
diketone IV in 7 ml of ethanol was added 0.35 g
(5 mmol) of hydroxylamine hydrochloride in 3 ml of
water. The reaction mixture was heated for 6 h,
cooled, and the crystalline precipitate (fine needles)
was filtered off.
19. Hunig, S. and Buysch, H.J., Chem. Ber., 1967,
vol. 100, no. 12, pp. 4017 4026.
20. Sokolovskaya, S.V. and Maevskii, Yu.V., Dep.
VINITI, Moscow, 1984, no. 920khp-84.
21. Kaga, Harumi, Miura, Maura, Masakatsu, and
Orito, Kazuhiko, Synthesis (BRD), 1989, no. 11,
pp. 864 866.
22. Makarova, N.V., Moiseev, I.K., and Zemtso-
va, M.N., Zh. Obshch. Khim., 1999, vol. 69, no. 4,
pp. 701 702.
23. Yagrushkina, I.N., Zemtsova, M.N., Klimoch-
kin, Yu.N., and Moiseev, I.K., Zh. Org. Khim.,
1994, vol. 30, no. 6, pp. 842 845.
24. Yagrushkina, I.N., Zemtsova, M.N., and Moise-
ev, I.K., Zh. Org. Khim., 1994, vol. 30, no. 7,
pp. 1072 1073.
25. Makarova, N.V., Zemtsova, M.N., and Moise-
ev, I.K., Khim. Geterotsiklo. Soed., 1994, no. 5,
pp. 621 623.
26. Makarova, N.V., Zemtsova, M.N., and Moise-
ev, I.K., Khim. Geterotsikl. Soed., 1994, no. 8,
pp. 1038 1040.
3-(1-Adamantyl)-2-phenyl-2,4,5,6-tetrahydro[c]-
pyrazole (X). A mixture of 0.5 g (2 mmol) of di-
ketone IV, 0.24 ml (2.5 mmol) of phenylhydrazine,
and 10 ml of ethanol was refluxed for 6 h. The
precipitate separated on cooling was filtered off and
washed with cold ethanol.
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