Reactions of 2-acylthiazolium salts with N-arylhydroxylamines

Tetrahedron

Volumn 55, Issue 12, 1999, Pages 3541-3552

  Ferreira, Luísa M ^a   Lobo, Ana M ^a   Prabhakar, Sundaresan ^a   Teixeira, Antonieta C ^a  

^a UNINOVA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; FOSENAZIDE; HYDROXYLAMINE; NITROGEN; SODIUM CHLORIDE;

ACETYLATION; ALKYLATION; ARTICLE; BIOTRANSFORMATION; CARCINOGENESIS; CARCINOGENICITY; MASS SPECTROMETER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033583302     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01161-2     Document Type: Article

References (31)

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13. +2 in the reaction medium. The interplay of these factors makes it difficult to propose a general mechanism for the generation of these nitrogen containing compounds under differing conditions. For mechanistic considerations involving some of the factors mentioned above, see: Novak, M.; Lagerman, R. K. J. Org. Chem. 1988, 55, 4762-4767; Boche, G.; Meir, C.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1777-1780; Novak, M.; Martin, K. A.; Heinrich, J. L.; Peet, K. M.; Mohler, L. K. J. Org. Chem. 1990, 55, 3023-3028; Helmick, J. S.; Novak, M. J. Org. Chem. 1991, 56, 2925-2927; Pereira, M. M. M. A. Ph.D. Thesis, New University of Lisbon 1992.
14. +2 in the reaction medium. The interplay of these factors makes it difficult to propose a general mechanism for the generation of these nitrogen containing compounds under differing conditions. For mechanistic considerations involving some of the factors mentioned above, see: Novak, M.; Lagerman, R. K. J. Org. Chem. 1988, 55, 4762-4767; Boche, G.; Meir, C.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1777-1780; Novak, M.; Martin, K. A.; Heinrich, J. L.; Peet, K. M.; Mohler, L. K. J. Org. Chem. 1990, 55, 3023-3028; Helmick, J. S.; Novak, M. J. Org. Chem. 1991, 56, 2925-2927; Pereira, M. M. M. A. Ph.D. Thesis, New University of Lisbon 1992.
15. +2 in the reaction medium. The interplay of these factors makes it difficult to propose a general mechanism for the generation of these nitrogen containing compounds under differing conditions. For mechanistic considerations involving some of the factors mentioned above, see: Novak, M.; Lagerman, R. K. J. Org. Chem. 1988, 55, 4762-4767; Boche, G.; Meir, C.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1777-1780; Novak, M.; Martin, K. A.; Heinrich, J. L.; Peet, K. M.; Mohler, L. K. J. Org. Chem. 1990, 55, 3023-3028; Helmick, J. S.; Novak, M. J. Org. Chem. 1991, 56, 2925-2927; Pereira, M. M. M. A. Ph.D. Thesis, New University of Lisbon 1992.
16. +2 in the reaction medium. The interplay of these factors makes it difficult to propose a general mechanism for the generation of these nitrogen containing compounds under differing conditions. For mechanistic considerations involving some of the factors mentioned above, see: Novak, M.; Lagerman, R. K. J. Org. Chem. 1988, 55, 4762-4767; Boche, G.; Meir, C.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1777-1780; Novak, M.; Martin, K. A.; Heinrich, J. L.; Peet, K. M.; Mohler, L. K. J. Org. Chem. 1990, 55, 3023-3028; Helmick, J. S.; Novak, M. J. Org. Chem. 1991, 56, 2925-2927; Pereira, M. M. M. A. Ph.D. Thesis, New University of Lisbon 1992.
17. +2 in the reaction medium. The interplay of these factors makes it difficult to propose a general mechanism for the generation of these nitrogen containing compounds under differing conditions. For mechanistic considerations involving some of the factors mentioned above, see: Novak, M.; Lagerman, R. K. J. Org. Chem. 1988, 55, 4762-4767; Boche, G.; Meir, C.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1777-1780; Novak, M.; Martin, K. A.; Heinrich, J. L.; Peet, K. M.; Mohler, L. K. J. Org. Chem. 1990, 55, 3023-3028; Helmick, J. S.; Novak, M. J. Org. Chem. 1991, 56, 2925-2927; Pereira, M. M. M. A. Ph.D. Thesis, New University of Lisbon 1992.
18. 3) and a pair of doublets, 2H each, at δ 7.09 (J = 8 Hz) and 6.90 (J = 8 Hz) due to 7Ad. A similar obervation was recorded for a mixture of 6d and acetyl cyanide, under the same conditions.
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21. The nitroso compound that is formed in this reaction is not likely to remain unaltered under these conditions since, in addition to giving rise to the corresponding azoxy derivative 8d, it would be expected to react rapidly with 18 to furnish a nitrone (vide ref. 18).
22. 3N, 3A rapidly acetylates 17 to 18, with simultaneous formation of 23.
23. We thank one of the referees for enabling us to refine certain steps in the mechanism proposed.
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