€
N. Coxskun, A. Oztu€rk / Tetrahedron 62 (2006) 12057–12063
12063
3873–3905; (e) Martin, J. N. Jones, R. C. F., Nitrones.
In Synthetic Applications of 1,3-Dipolar Cycloaddition
Chemistry Toward Heterocycles and Natural Products; The
Chemistry of Heterocyclic Compounds; Wiley: Chichester,
UK, 2002; Vol. 59, pp 1–81.
J¼7.41), 1.61 (2H, hex, J¼7.41), 3.34 (2H, m), 3.63 (3H, s),
3.81 (3H, s), 3.83 (3H, s), 4.25 (1H, d, J¼13.3), 4.52 (1H, d,
J¼13.3), 6.31 (1H, s), 6.85 (1H, m), 6.86–7.02 (2H, m),
7.37–7.77 (4H, m), 9.40 (1H, s); 13C NMR (100 MHz,
CDCl3): d 11.7; 22.5; 41.8; 53.1; 56.0; 57.8; 61.2; 68.1;
107.0; 112.7; 123.5; 124.2; 124.3; 128.5; 129.0; 130.1;
133.6; 135.6; 148.1; 148.6; 152.9; 156.4; 157.1; 164.9.
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2. (a) Coxskun, N.; Sumengen, D. Synth. Commun. 1993, 23, 1699–
1706; (b) Coxskun, N.; Asutay, O. Chim. Acta Turc. 1997, 25,
69–72; (c) Coxskun, N.; Asutay, O. Chim. Acta Turc. 1999, 27,
17–23.
Anal. Calcd for C24H27N3O8 (485.49): C, 59.37; H, 5.61; N,
8.66. Found: C, 59.39; H, 5.63; N, 8.73.
3. (a) Coxskun, N. Tetrahedron Lett. 1997, 38, 2299–2302; (b)
Coxskun, N. Tetrahedron 1997, 53, 13873–13882; (c) Coxskun,
N.; Ay, M. Heterocycles 1998, 48, 537–544; (d) Coxskun, N.;
4.3.6. 2-(2,3-Dimethoxybenzyl)-3-phenyl-5-propylcarba-
moyl-2,3-dihydroisoxazole-4-carboxylic acid methyl
ester 3g. Yield 42%; oil; IR (KBr) nC]O 1691, 1672, nNH
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¨
€
€
Tat, F. T.; Guven, O. O.; Ulku, D.; Arıcı, C. Tetrahedron Lett.
€ €
2000, 41, 5407–5409; (e) Coxskun, N.; Tat, F. T.; G€uven, O. O.
1
3280 cmꢀ1; H NMR (400 MHz, CDCl3): d 0.98 (3H, t,
Tetrahedron 2001, 57, 3413–3417; (f) Coxskun, N.; Yılmaz, B.
Synth. Commun. 2004, 34, 1617–1623; (g) Coxskun, N.; Tat,
J¼7.5), 1.63 (2H, hex, J¼7.5), 3.40 (2H, m), 3.63 (3H, s),
3.76 (3H, s), 3.85 (3H, s), 4.24 (1H, d, J¼12.9), 4.43 (1H,
d, J¼12.9), 5.35 (1H, s), 6.86 (1H, m), 7.00 (2H, m),
7.19–7.25 (5H, m), 9.69 (1H, s); 13C NMR (100 MHz,
CDCl3): d 11.8; 22.5; 41.8; 52.5; 56.0; 57.0; 61.3; 73.7;
107.3; 112.4; 123.5; 124.3; 127.6; 128.2; 128.6; 128.8;
140.8; 148.1; 152.9; 156.1; 156.8; 166.0.
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F. T.; G€uven, O. O. Tetrahedron: Asymmetry 2001, 12, 1463–
1467; (h) Coxskun, N.; Tunc¸man, S. Tetrahedron 2006, 62,
1345–1350.
4. (a) Coxskun, N. Turk. J. Chem. 2001, 25, 267–272; (b) Coxskun,
N.; Tat, F. T. Phosphorus Sulfur 2003, 178, 881–886; (c)
Coxskun, N.; Tat, F. T. Turk. J. Chem. 2004, 28, 1–7.
5. Freeman, J. P. Chem. Rev. 1983, 83, 241–261.
6. Jones, R. C. F.; Martin, J. N.; Smith, P.; Gelbrich, T.; Light,
M. E.; Hursthouse, M. B. Chem. Commun. 2000, 1949–1950.
7. (a) Habeeb, A. G.; Praveen Rao, N. P.; Knaus, E. E. J. Med.
Chem. 2001, 44, 2921–2927; (b) Ishikawa, T.; Kudoh, T.;
Yoshida, J.; Yasuhara, A.; Manabe, S.; Saito, S. Org. Lett.
2002, 4, 1907–1910; (c) Chiacchio, U.; Rescifina, A.;
Chiacchio, M. A.; Romeo, G.; Romeo, R. J. Org. Chem.
2003, 68, 3718–3720.
8. Coxskun, N.; Parlar, A. Synth. Commun. 2005, 35, 2445–2451.
9. (a) Vedejs, E.; Naidu, B. N.; Klapars, A.; Warner, D. L.; Li,
V. S.; Na, Y.; Kohn, H. J. Am. Chem. Soc. 2003, 125, 15796–
15806; (b) Vedejs, E.; Piotrowski, D. W.; Tucci, F. C. J. Org.
Chem. 2000, 65, 5498–5505.
Anal. Calcd for C24H28N2O6 (440.49): C, 65.44; H, 6.41; N,
6.36. Found: C, 65.45; H, 6.48; N, 6.31.
4.3.7. 4-Hydroxy-1-(methoxyphenylmethyl)-5-oxo-
2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid
methyl esters 10 and 11. Yield 55%; mp 132 ꢁC; IR (KBr)
1
nC]O 1694; 1678, nOH 3282 cmꢀ1; H NMR (400 MHz,
CDCl3): d 3.13 (3H, s, CHOMe), 3.45 (3H, s, CHOMe),
3.56 (3H, s, CO2Me), 3.62 (3H, s, CO2Me), 4.71 (1H, s,
C-3H), 5.27 (1H, s, C-3H), 6.40 (2H, s, MeOCHN), 6.76–
6.78 (2H, m), 6.87–6.94 (6H, m), 7.00–7.03 (3H, m), 7.22–
7.29 (6H, m), 7.36–7.38 (3H, m), 9.0 (2H, br s, OH); 13C
NMR (100 MHz, CDCl3): d 52.2, MeO, ether; 52.2, MeO,
ester; 56.1, MeO, ester; 57.0, MeO, ester; 57.8, C-3; 58.4,
C-3, 84.28, NCO; 84.33, NCO; 114.1, C-4; 114.6, C-4;
126.2; 126.5; 127.7; 127.8; 127.9; 128.0; 128.4; 128.6;
128.7; 128.8; 134.9; 135.8; 136.3; 137.7; 156.5, C-5; 156.6,
C-5; 165.6, C]O, 165.7, C]O; 165.8, C]O; 165.9, C]O.
10. (a) Venkov, A. P.; Vodenicharov, D. M. Synthesis-Stuttgart
1990, 253–255; (b) Coxskun, N.; Tirli, F. T. Synth. Commun.
1997, 27, 1–9; (c) Coxskun, N.; Buyukuysal, L. Heterocycles
1998, 48, 53–59; (d) Coxskun, N.; Kızılkuxsak, Y. T. Synth.
Commun. 2005, 35, 2435–2443.
11. (a) Mesnard, F.; Girard, S.; Fliniaux, O.; Bhogal, R. K.; Gillet,
F.; Lebreton, J.; Fliniaux, M. A.; Robins, R. J. Plant Sci. 2001,
161, 1011–1018; (b) Sunagawa, M.; Matsumura, H.; Inoue, T.;
Fukasawa, M.; Kato, M. J. Antibiot. 1990, 43, 519–532; (c) Iso,
Y.; Irie, T.; Nishino, Y.; Motokawa, K.; Nishitani, Y. J. Antibiot.
1996, 49, 199–209; (d) Imamura, H.; Shimizu, A.; Sato, H.;
Sugimoto, Y.; Sakuraba, S.; Nakajima, S.; Abe, S.; Miura,
K.; Nishimura, I.; Yamada, K.; Morishima, H. Tetrahedron
2000, 56, 7705–7713.
12. (a) Matkhalikova, S. F.; Malikov, V. M.; Yunusov, S. Y. Khim.
Prir. Soedin. 1969, 5, 606–607; (b) Matkhalikova, S. F.;
Malikov, V. M.; Yunusov, S. Y. Khim. Prir. Soedin. 1969, 5,
30–32.
Anal. Calcd for C20H19NO5 (353.37): C, 67.98; H, 5.42; N,
3.96. Found: C, 67.95; H, 5.40; N, 3.93.
Acknowledgements
˘
Uludag University Research Fund and Turkish State Plan-
ning Organization (DPT) are gratefully acknowledged for
the financial support (Project No. 2001-2).
References and notes
13. Chandrasekhar, S.; Jagadeshwar, V.; Prakash, S. J. Tetrahedron
Lett. 2005, 46, 3127–3129.
14. Coxskun, N.; Er, M. Tetrahedron 2003, 59, 3481–3485.
15. Coxskun, N.; Er, M. Turk. J. Chem. 2005, 29, 455–461.
1. (a) Black, D. St. C.; Crozier, R. F.; Davis, V. C. Synthesis 1975,
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