Reductive deamination of aromatic amines with nitric oxide (NO)

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4165-4168

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

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; AROMATIC AMINE; AROMATIC COMPOUND; CHLOROFORM; DIAZONIUM COMPOUND; NITRIC OXIDE; TETRAHYDROFURAN;

ARTICLE; DEAMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0029895876     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00785-X     Document Type: Article

References (23)

1. This paper is dedicated to Professor Masaaki Hirobe on the occasion of his 60th birthday.
2. a) Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109-142.
3. b) Stamler, J. S.; Singel, D. J.; Loscalzo, J. Science, 1992, 258, 1898-1902.
4. c) Feldman, P. L.; Griffith, O. W.; Stuehr, D. J. Chem. Eng. News, 1993, Dec 20, 26-38.
5. Hayakawa, H.; Hirata, Y.; Suzuki, E.; Kimura, K.; Kikuchi, K.; Nagano, T.; Hirobe, M.; Omata, M. Hypertension, 1994, 23, 752-756, and references cited therein.
6. Durante, W.; Kroll, M. H.; Vanhoutte, P. M.; Schafer, A. I. Blood, 1992, 79, 110-116.
7. Warren, J. B.; Coughlan, M. L.; Williams, T. J. Br. J. Pharmacol., 1992, 106, 953-957, and references cited therein.
8. a) Wilcox, A. L.; Janzen, E. J. J. Chem. Soc., Chem. Commun. 1993, 1377-1379.
9. b) Janzen, E. G.; Wilcox, A. L.; Manoharan, V. J. Org. Chem. 1993, 58, 3597-3599.
10. Itoh, T.; Nagata, K.; Okada, M.; Ohsawa, A. Tetrahedron Lett. 1995, 36, 2269-2272.
11. a) Mukaiyama, T.; Hata, E.; Yamada, T. Chem. Lett. 1995, 505-506.
12. b) Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3629-3636.
13. a) de la Breteche, M.-L.; Servy, C.; Lenfant, M.; Ducrocq, C. Tetrahedron Lett., 1994, 35, 7231-7232.
14. b) d'Ischia, M.; Constantini, C. BioMed. Chem. 1995, 3, 923-927.
15. d'Ischia, M. Tetrahedron Lett. 1995, 36, 8881-8884.
16. Nagano, T.; Takizawa, H.; Hirobe, M. Tetrahedron Lett. 1995, 36, 8239-8242.
17. PM3 calculations suggest that m-methoxy and m-methylthiophenyl radicals are more stable as compared to the corresponding o-and p-isomers, thus the reason for this substituent effect remains unclear.
18. When methyl phenyl sulfide was allowed to react with NO (20 eq.) in DCE under Ar for 15 h, methyl phenyl sulfoxide was obtained in a quantitative yield. Use of other solvents such as THF, DME, and MeOH, resulted in a complete recovery of the substrate.
19. In the case of 1a as a substrate, relationships between the amount of NO, the reaction time, and the yield are as follows; 84% (NO 20 eq. 2 h); 81% (NO 10 eq. 20 h); 80% (NO 5 eq. 30 h); 70% (NO 4 eq. 67 h); 56% (NO 3 eq. 240 h).
20. a) Brown Jr, J. F. J. Am. Chem. Soc. 1957, 79, 2480-2488.
21. b) Tuaillon, J.; Perrot, R. Helv. Chim. Acta. 1978, 61, 558-566.
22. Westheimer, F. H.; Segel, E.; Schramn, R. J. Am. Chem. Soc. 1947, 69, 773-785.
23. In THF, the nitration reported in ref.8 was slow; therefore, 4,4-diaminostilbene was deaminated by NO without nitration of the double bond moiety. The detailed results will be reported in the near future.