One-pot synthesis of N-imidoylbenzotriazoles via benzotriazole-mediated Beckmann rearrangement of oximes

Organic Letters

Volumn 1, Issue 4, 1999, Pages 577-578

  Katritzky, Alan R ^a   Monteux, Daphne A ^a   Tymoshenko, Dmytro O ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000130116     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990090g     Document Type: Article

References (21)

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4. (b) McCarty, C. G. In Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Wiley-Interscience: New York, 1970; p 408.
5. (a) Hattori, K.; Matsumura, Y.; Miyazaki, T.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 7368.
6. (b) Hattori, K.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 3395.
7. Oxley, P.; Short, W. F. J. Chem. Soc. 1948, 1514.
8. Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831.
9. Ishida, Y.; Sasatani, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 3255.
10. Yokomatsu, T.; Minowa, T.; Yoshida, Y.; Shibuya, S. Heterocycles 1997, 44, 111.
11. Matsumura, Y.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 6312.
12. Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
13. Katritzky, A. R.; Rachwal, S.; Offerman, R. J.; Najzarek, Z.; Yagoub, A. K.; Zhang, Y. Chem. Ber. 1990, 1545.
14. Katritzky, A. R.; Stevens, C. V.; Zhang, G.-F.; Jiang, J. Heterocycles 1995, 40, 231.
15. Katritzky, A. R.; Yang, B.; Abonia, R.; Insuasty, B. J. Chem. Res. 1996, 540.
16. Katritzky, A. R.; Zhana, G.-F.; Wu, J. J. Synth. Commun. 1994, 24, 205.
17. Ried, W.; Schon. M. Chem. Ber. 1965, 3142.
18. Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412.
19. 10
20. The protons on the phenyl group have been identified based on their intensity and multiplicity as 7.38 (d. 2H) ortho and 7.32 (t, 2H) meta. The para proton is at 7.39, as demonstrated by the intensity of the cluster around 7.38 and by the lack of couplings of 7.38-7.39 and 7.32 to any other protons but themselves. The long-range coupling between 7.32 and 130.4 identified the quaternary carbon on the phenyl ring, and the long-range coupling of 7.38 to 156.0 identified the imine carbon and demonstrated that the phenyl is attached to the carbon of the imine group. The quaternary carbon at 146.4 was assigned to position 3a of benzotriazole on the basis of its chemical shift. Long-range couplings identified the protons meta to this carbon as 8.53 (d, position 7) and 7.50 (t, position 5). The protons in positions 4 and 6 were identified as 8.14 and 7.62, correspondingly, on the basis of their couplings to the other protons on the Bt. Long-range couplings of 8.14 and 7.62 allowed the assignment of the quaternary carbon in position 7a as 131.8. The CH at 8.34/148.8 was assigned to position 6 of the pyridine, based on the chemical shifts. The tocsy spectrum revealed the sequence 8.34-6.94-7.53-6.73. The H-C long-range couplings confirmed this assignment and revealed the quaternary carbon in position 2 as 159.7.
21. 4, and the solvent was removed under reduced pressure. The residue was subjected to purification (method A, extraction with hot hexanes; method B, flash column chromatography).