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X. Jia et al. / Tetrahedron 65 (2009) 2334–2338
EIMS m/z (rel int., %): 135 (2.1), 138 (4.9), 100 (100), 58 (98.8).
ESI-HRMS m/z calcd for C13H18N2O2þNa: 257.1260; found: 257.1262.
13C NMR (75 MHz, CDCl3): rotamer A (major):
d 17.4, 21.6, 25.1, 86.6,
111.9, 117.6, 136.8, 143.3, 144.5; 170.8; rotamer B (minor):
22.0, 27.9, 82.1, 111.9, 117.5, 136.9, 143.1, 144.7, 170.8.
EIMS m/z (rel int., %): 111 (1.6), 100 (77.8), 58 (100).
d 16.3,
4.3.14. (E)-O-1-(N-Acetamino-1-yl)ethyl-4-methylbenzaldehyde
oxime (11i)
ESI-HRMS m/z calcd for C10H14N2O3þNa: 233.0897; found:
233.0899.
1H NMR (300 MHz, CDCl3):
d
1.50 (d, J¼6.0 Hz, 3H), 2.01 (s, 3H), 2.35
4.3.18. (E)-O-1-(N-Methyl-N-methylacetamino-1-yl)ethyl-2-
pyridinecarboxaldehyde oxime (11m)
(s, 3H), 6.00–6.05 (m, 1H), 6.36 (br, 1H), 7.16 (d, J¼8.0 Hz, 2H), 7.46
(d, J¼8.0 Hz, 2H), 8.02 (s, 1H).
1H NMR (300 MHz, CDCl3): rotamer A (major):
d
1.45 (d, J¼6.0 Hz,
13C NMR (75 MHz, CDCl3):
d 19.8, 21.4, 23.4, 79.7, 127.0, 129.3, 140.1,
149.5, 169.6 (one 13C signal lost for overlap).
3H), 2.44 (s, 3H), 2.75 (s, 3H), 5.85 (q, J¼6.0 Hz, 1H), 7.17–7.21 (m,
1H), 7.56–7.61 (m, 1H), 7.62 (d, J¼7.5 Hz, 1H), 8.08–8.09 (m, 1H),
EIMS m/z (rel int., %): 135 (1.0), 103 (1.3), 86 (21.7), 44 (100).
ESI-HRMS m/z calcd for C12H16N2O2þNa: 243.1104; found: 243.1106.
8.50 (s, 1H); rotamer B (minor):
d
1.33 (d, J¼6.3 Hz, 3H), 2.23 (s, 3H),
2.79 (s, 3H), 6.57 (q, J¼6.3 Hz, 1H), 7.17–7.21 (m, 1H), 7.56–7.61 (m,
1H), 7.78 (d, J¼7.8 Hz, 1H), 8.08–8.09 (m, 1H), 8.51 (s, 1H).
13C NMR (75 MHz, CDCl3): rotamer A (major):
d 17.4, 21.8, 25.2, 86.5,
4.3.15. (E)-O-1-(N-Formamino-1-yl)ethyl-4-methylbenzaldehyde
120.4, 124.1, 136.3, 149.3, 150.4, 151.0, 170.9; rotamer B (minor):
16.4, 22.2, 28.2, 82.1, 120.6, 124.1, 136.3, 149.5, 150.6, 151.3, 170.9.
EIMS m/z (rel int., %): 122 (6.3), 100 (78.6), 58 (100).
ESI-HRMSm/zcalcd for C11H15N3O2þNa:244.1056; found:244.1048.
oxime (11j)
d
1H NMR (300 MHz, CDCl3):
d
1.52 (d, J¼5.2 Hz, 3H), 2.34 (s, 3H), 5.47
(q, J¼5.2 Hz, 1H), 6.08 (br, 1H), 7.15 (d, J¼8.0 Hz, 2H), 7.43 (d,
J¼8.0 Hz, 2H), 7.99 (s, 1H), 8.38 (s, 1H).
13C NMR (75 MHz, CDCl3):
160.5, 165.4.
d 19.2, 21.4, 82.7,127.1,129.0,140.2,149.8,
References and notes
EIMS m/z (rel int., %): 206 (2.1), 135 (14.9), 72 (78.8), 44 (100).
ESI-HRMS m/z calcd for C11H14N2O2þNa: 229.0950; found:
229.0950.
1. (a) Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6745;
(b) Hanessian, S.; Lu, P. P.; Sanceau, J. Y.; Chemla, P.; Gohda, K.; Fonne-Pfiser, R.;
Prade, L.; Cowan-Jacob, S. W. Angew. Chem., Int. Ed. 1999, 38, 3159; (c) Bernardi,
L.; Cere, V.; Femoni, C.; Pollicino, S.; Ricci, A. J. Org. Chem. 2003, 68, 3348; (d)
Kakiya, H.; Yagi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2002, 124, 9032;
(e) Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. Synlett 1997, 659; (f) Marco, J. A.;
Carda, M.; Murga, J.; Gonzalez, F.; Falomir, E. Tetrahedron Lett. 1997, 38, 1841.
2. (a) Kim, S.; Song, H. J.; Choi, T. L.; Yoon, J. Y. Angew. Chem., Int. Ed. 2001, 40, 2524;
(b) Miyabe, H.; Ueda, M.; Yashioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000,
56, 2413; (c) Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131;
(d) Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 2000, 1789; (e) Miyabe, H.;
Ueda, M.; Naito, T. Synlett 2004, 1140; (f) Mcnabb, S. B.; Ueda, M.; Naito, T. Org.
Lett. 2004, 6, 1911; (g) Ryu, I.; Kuriyama, H.; Minakata, S.; Komatsu, M.; Yoon, J.-
Y.; Kim, S. J. Am. Chem. Soc. 1999, 121, 12190.
3. (a) Bull, S. D.; Davies, S. G.; Domingez, S. H.; Jones, S.; Price, A. J.; Sellers, T. G. R.;
Thomas, G. R.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2002, 2141; (b) Davis, S.
G.; Fox, J. F.; Jones, S.; Price, A. J.; Sanz, M. A.; Sellers, T. G. R.; Smith, A. D.;
Teixeira, F. C. J. Chem. Soc., Perkin Trans. 1 2002, 1757; (c) Koenig, S. G.; Leonard, K.
A.; Lowe, R. S.; Austin, D. J. Tetrahedron Lett. 2000, 41, 9393.
4. (a) Miyabe, H.; Matsumura, A.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. Synlett
2004, 2123; (b) Miyabe, H.; Yoshida, K.; Reddy, V. K.; Matsumura, A.; Takemoto,
Y. J. Org. Chem. 2005, 70, 5630; (c) Miyabe, H.; Matsumura, A.; Moriyama, K.;
Takemoto, Y. Org. Lett. 2004, 6, 4631.
4.3.16. (E)-O-1-(N-Methyl-N-acetamino-1-yl)ethylacetophenone
oxime (11k)
1H NMR (300 MHz, CDCl3): rotamer A (major):
3H), 2.10 (s, 3H), 2.18 (s, 3H), 2.70 (s, 3H), 5.78 (q, J¼6.3 Hz, 1H),
7.19–7.21 (m, 3H), 7.43–7.54 (m 2H); rotamer B (minor): 1.28 (d,
d
1.38 (d, J¼6.3 Hz,
d
J¼6.3 Hz, 3H),1.94 (s, 3H), 2.10 (s, 3H), 2.70 (s, 3H), 6.51 (q, J¼6.3 Hz,
1H), 7.19–7.21 (m, 3H), 7.43–7.54 (m, 2H).
13C NMR (75 MHz, CDCl3): rotamer A (major):
d
11.8, 17.4, 21.6, 28.0,
85.8, 127.9, 128.8, 128.9, 135.6, 155.2, 170.1; rotamer B (minor):
12.0, 16.4, 22.0, 28.0, 81.5, 125.6, 127.9, 128.8, 135.6, 154.7, 170.7.
d
EIMS m/z (rel int., %): 135 (2.2), 118 (5.6), 100 (100), 58 (99.9).
ESI-HRMS m/z calcd for C13H18N2O2þNa: 257.1260; found:
257.1263.
5. Bhuniya, D.; Moban, S.; Narayanan, S. Synthesis 2003, 1018.
6. De, P.; Nonappa; Pandurangan, K.; Maitra, U.; Wailes, S. Org. Lett. 2007, 9, 2767.
7. (a) Jia, X. D.; Lin, H. C.; Huo, C. D.; Zhang, W.; Lu¨, J. M.; Yang, L.; Zhao, G. Y.; Liu, Z.
L. Synlett 2003, 1707; (b) Jia, X. D.; Han, B.; Zhang, W.; Jin, X. L.; Yang, L.; Liu, Z. L.
Synthesis 2006, 2831; (c) Jia, X. D.; Da, Y. X.; Yang, C. X.; Yang, L.; Liu, Z. L. Tet-
rahedron Lett. 2008, 49, 1786; (d) Huo, C. D.; Jia, X. D.; Zhang, W.; Yang, L.; Lu¨, J.
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Tetrahedron 2005, 61, 1325.
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9. Schoenewaldt, E. F.; Kinnel, R. B.; Paul, D. J. Org. Chem. 1968, 33, 4270.
4.3.17. (E)-O-1-(N-Methyl-N-acetamino-1-yl)ethyl-2-furaldehyde
oxime (11l)
1H NMR (300 MHz, CDCl3): rotamer A (major):
3H), 2.18 (s, 3H), 2.71 (s, 3H), 5.83 (q, J¼6.0 Hz,1H), 6.43 (s,1H), 7.10–
7.12 (m, 1H), 7.33 (s, 1H), 7.38 (s, 1H); rotamer B (minor): 1.36 (d,
d
1.48 (d, J¼6.0 Hz,
d
J¼6.3 Hz, 3H), 2.02 (s, 3H), 2.74 (s, 3H), 6.43 (s,1H), 6.69 (q, J¼6.3 Hz,
1H), 7.10–7.12 (m, 1H), 7.33 (s, 1H), 7.38 (s, 1H).