1814
M. P. Sadashiva et al. / Bioorg. Med. Chem. Lett. 15 (2005) 1811–1814
The E/Z isomers mixture (yellow oil, 0.57 g, 51%) was
obtained from nitrobenzene 7 (0.41 mL, 4.06 mmol)
(KBr): 3247, 3062, 2959, 2873, 1730, 1598, 1258, 1085,
825, 757, 694, 598 cmꢀ1. Anal. Calcd CHN: 62.14,
6.95, 10.35. Found: 62.19, 7.06, 10.38.
and 2-butyl-4-chloro-1H-imidazolyle aldehyde
1
(0.75 g, 4.02 mmol). 1H NMR (CDCl3, 400 MHz): d
0.76 (t, 3H, CH3), 0.93 (t, 3H, CH3), 1.11 (m, 2H,
CH2), 1.38 (m, 2H, CH2), 1.49 (m, 2H, CH2), 1.75 (m,
2H, CH2), 2.36 (t, 2H, CH2), 2.75 (t, 2H, CH2), 7.32
(s, 1H, CH@N), 7.32–7.48 (Ar-H, merged with isomer),
7.97 (s, 1H, CH@N), 12.13 (br s, 1H, NH), 12.72 (br s,
1H, NH). IR (KBr): 3045, 2863, 2857, 1548, 1176, 893,
740, 660 cmꢀ1. Anal. Calcd CHN: 60.54, 5.81, 15.13.
Found: 60.63, 5.84, 15.18.
Acknowledgements
We are grateful to the University of Mysore, Mysore,
India for financial support under the UPG-JRF order
No. DV-5/57/U.P.G.F./2003–2004. The CHNS and
UV–Vis data obtained from this department with equip-
ments funded by DST-FIST (No. SR/FST/CSI-051/
2002. Dated 28.7.2003) grant.
5.2.2.
E-C-(2-Butyl-4-chloro-1H-imidazolyl)-N-phenyl
nitrone (4, E > 98% ee). This compound was obtained
by condensation aldehyde 1 (0.5 g, 2.68 mmol) and phe-
nyl hydroxylamine hydrochloride 2 (0.39 g, 2.68 mmol)
in the presence of Bronsted acid/MgCl2 catalyst. The
yellow solid (0.49 g, 67.2%) melted at 42–44 ꢁC. 1H
NMR (CDCl3, 400 MHz): d 0.93 (t, 3H, CH3), 1.38
(m, 2H, CH2), 1.75 (m, 2H, CH2), 2.75 (t, 2H, CH2),
7.32–7.72 (Ar-H, 5H), 7.97 (s, 1H, CH@N), 12.72 (br
s, 1H, NH). IR (KBr): 3045, 2863, 2857, 1548, 1176,
893, 740, 660 cmꢀ1. Anal. Calcd CHN: 60.54, 5.81,
15.13. Found: 60.63, 5.84, 15.18.
References and notes
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1998, 36(Suppl 1), 119.
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1625.
4. Ghannooun, M. A.; Rice, L. B. Clin. Microbiol. Res. 1999,
12, 501.
5. Graybill, J. R. Clin. Infect. Dis. 1992, 14(Suppl 1), S170.
6. Rinaldi, M. G. Clin. Infect. Dis. 1992, 14(Suppl 1), S130.
7. Walsh, T. J. Hematol. Oncol. Clin. North Am. 1993, 7,
1003.
8. Warnock, D. W. J. Antimicrob. Chemther. 1995, 36(Suppl
B), 73.
9. Georgopapadakou, N. H. Antimicrob. Agents Chemother.
1996, 40, 279.
10. Saeed Emami; Mehraban Falahati; Ali Banifatemi; Mas-
soud Amanlou; Abba shafiee Bioorg. Med. Chem. 2004,
12, 3971.
5.2.3. Procedure for the synthesis of 2-(phenyl)-3-(2-
butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine. A
mixture of 4 and butyl acrylate in toluene was refluxed
until reaction completes monitored by TLC. The reac-
tion mixture was cooled to room temperature and
concentrated under reduced pressure. The major
regioisomer 5/50 was separated on silica gel column by
eluting with hexane/ethylacetate (9:1).
11. Graybill, J. R. Clin. Infec. Dis. 1992, 22(Suppl 2), S166.
12. Ravikumar, K. R.; Mallesha, H.; Basappa; Rangappa,
K. S. Eur. J. Med. Chem. 2003, 38, 163.
13. Ravikumar, K. R.; Mallesha, H.; Rangappa, K. S. Synth.
Commun. 2003, 33, 1545.
14. Ravikumar, K. R.; Mallesha, H.; Basappa; Rangappa,
K. S. J. Heterocycl. Chem. 2003, 40, 607.
15. Ravikumar, K. R.; Mallesha, H.; Rangappa, K. S. Arch.
Pharm. Med. Chem. 2003, 336, 159.
16. Sadashiva, M. P.; Mallesha, H.; Hithesh, N. A.; Rang-
appa, K. S. Bioorg. Med. Chem. 2004, 12, 6389.
17. McDougal, Nolan T.; Schaus, Scott E. J. Am. Chem. Soc.
2003, 125, 12094–12095.
The isomer A: 1H NMR (CDCl3, 400 MHz): d 0.74–1.08
(m, 6H, CH3), 1.11–1.49 (m, 4H, CH2), 1.59–1.75 (m,
4H,CH2), 2.66 (t, 2H, CH2), 2.43 (ddd, 1H, H4a,
J = 13.4, 5.87, 4.7 Hz), 2.30 (ddd, H4b, J = 13.28, 7.96,
5.3 Hz), 3.08 (t, 2H, OCH2), 4.84 (dd, 1H, CH,
J = 8.8, 5.4 Hz), 5.12 (dd, 1H, CH, J = 8.4, 4.7 Hz),
7.02 (t, 1H, Ar-H), 7.07 (d, 2H, Ar-H), 7.28 (t, 2H,
Ar-H), 10.46 (s, 1H, NH). IR (KBr): 3247, 3062, 2959,
2873, 1730, 1598, 1258, 1085, 825, 757, 694, 598 cmꢀ1
.
Anal. Calcd CHN: 62.14, 6.95, 10.35. Found: 62.19,
7.06, 10.38.
18. Beeranahally Doreswamy, H.; Basappa; Madegowda, M.;
Mantelingu, K.; Sridhar Anandalwar, M.; Javaregowda
Prasad; Rangappa, K. S. Anal. Sci. 2003, 19, 31.
19. Mallesha, H.; Ravikumar, K. R.; Vishukumar, B. K.;
Mantelingu, K.; Rangappa, K. S. Indian Acad. Sci. 2001,
113, 291.
20. Collins, C. H.; Lyne, P. M. Microb. Methods; Butter
worth: London, 1970, p 21.
21. (a) Elhance, D. N. Fundamental of Statistics; 30th ed.,
1984; (b) Coltan, T. Statistics in Medicine; 1st ed., 1974.
1
The isomer B: brownish thick liquid (59%). H NMR
(CDCl3, 400 MHz): d 0.81–1.01 (m, 6H, CH3), 1.22–
1.42 (m, 4H, CH2), 1.55–1.82 (m, 4H, CH2), 2.65 (t,
2H, CH2), 2.43 (ddd, 1H, H4a, J = 13.4, 5.87, 4.7 Hz),
2.99 (ddd, H4b, J = 13.28, 7.96, 5.3 Hz), 3.08 (t, 2H,
OCH2), 4.57 (dd, 1H, CH, J = 8.8, 5.4 Hz), 4.82 (dd,
1H, CH, J = 8.4, 4.7 Hz), 6.95–7.15 (m, 3H, Ar-H),
7.22–7.35 (m, 2H, Ar-H), 10.62 (br s, 1H, NH). IR