Reaction of Nitric Oxide with Amines

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3582-3585

  Itoh, Takashi ^a   Nagata, Kazuhiro ^a   Matsuya, Yûji ^a   Miyazaki, Michiko ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001190181     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962101e     Document Type: Article

References (41)

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12. 2, which was not added to the reaction mixtures deliberately, might bring about reactions of substrates with NO; see: (d) Challis, B. C.; Kyrtopoulos, S. A. J. Chem. Soc., Perkin Trans. 1 1979, 299. (e) Afzal, M.; Walton, J. C. BioMed. Chem. Lett. 1996, 6, 2329.
13. 2, which was not added to the reaction mixtures deliberately, might bring about reactions of substrates with NO; see: (d) Challis, B. C.; Kyrtopoulos, S. A. J. Chem. Soc., Perkin Trans. 1 1979, 299. (e) Afzal, M.; Walton, J. C. BioMed. Chem. Lett. 1996, 6, 2329.
14. 2, which was not added to the reaction mixtures deliberately, might bring about reactions of substrates with NO; see: (d) Challis, B. C.; Kyrtopoulos, S. A. J. Chem. Soc., Perkin Trans. 1 1979, 299. (e) Afzal, M.; Walton, J. C. BioMed. Chem. Lett. 1996, 6, 2329.
15. 2, which was not added to the reaction mixtures deliberately, might bring about reactions of substrates with NO; see: (d) Challis, B. C.; Kyrtopoulos, S. A. J. Chem. Soc., Perkin Trans. 1 1979, 299. (e) Afzal, M.; Walton, J. C. BioMed. Chem. Lett. 1996, 6, 2329.
16. 2, which was not added to the reaction mixtures deliberately, might bring about reactions of substrates with NO; see: (d) Challis, B. C.; Kyrtopoulos, S. A. J. Chem. Soc., Perkin Trans. 1 1979, 299. (e) Afzal, M.; Walton, J. C. BioMed. Chem. Lett. 1996, 6, 2329.
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25. 3 might be 1087 times higher (0.435 × 2500) than that of NO. The calculations using data of Table 2, entries 3 and 4, give the values 692 and 978, respectively.
26. 2 reacts at least 200 times as rapidly as NO with 7,7,8,8-tetramethyl-o-quinodimethane: Korth, H.-G.; Sustman, R.; Lommes, P.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. The result is in agreement in the order of magnitude with our estimation.
27. When 1 was methylated at N-1, it was inert to this reaction. Thus, we supposed that an initial hydrogen abstraction might not occur at the C-4 position.
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29. It was reported that phenyldiazonium salts that have an electron-donating group on the meta position were unstable compared to their o- or p-substituted counterparts. See: Swain, C. G.; Sheats, J. E.; Harbison, K. G. J. Am. Chem. Soc. 1975, 97, 783.
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31. The low yield of the azo product 8a suggests the possibility that all of the precipitate may not be the corresponding diazonium salt. Drago et al. have shown that primary and secondary amines reacted with NO at -78 °C in ether to form precipitates that were characterized as complexes of amines and NO: (a) Drago, R. S.; Paulik, F. E. J. Am. Chem. Soc. 1960, 82, 96. (b) Drago, R. S.; Karstetter, B. R. J. Am. Chem. Soc. 1961, 83, 1819. Our precipitate might comprise this type of complex, although it was reported in ref 19b that aniline did not form the stable one.
32. The low yield of the azo product 8a suggests the possibility that all of the precipitate may not be the corresponding diazonium salt. Drago et al. have shown that primary and secondary amines reacted with NO at -78 °C in ether to form precipitates that were characterized as complexes of amines and NO: (a) Drago, R. S.; Paulik, F. E. J. Am. Chem. Soc. 1960, 82, 96. (b) Drago, R. S.; Karstetter, B. R. J. Am. Chem. Soc. 1961, 83, 1819. Our precipitate might comprise this type of complex, although it was reported in ref 19b that aniline did not form the stable one.
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38. It was revealed that the same reaction process was applied to 2-aminothiazole and 3-amino-1,2,4-triazines, which gave poor results by the use of the conventional methods, to give the corresponding deamination products in good yields. The detailed results will be reported in a near future.
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