Halogenation of pyridinols using bis(sym-collidine)iodine(I) and bis(sym-collidine)bromine(I) hexafluorophosphate

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2467-2470

  Rousseau, Gérard ^a   Robin, Sylvie ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; PYRIDINOL;

ARTICLE; BROMINATION; CHEMICAL REACTION; DRUG SYNTHESIS; HALOGENATION; IODINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030980181     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00385-7     Document Type: Article

References (21)

1. Königs W., Geigy R. Ber. dtsch. chem. Ges. 17:1884;589-599.
2. 2-Pyridinol: a) Magidson, O.; Menshikoff, G. Ber. dtsch. chem. Ges. 1925, 58, 113-118. 3-Pyridinol: b) Koch, V.; Schnatterer, S. Synthesis 1990, 497-498. c) Clark,G.J.; Deady, L.W. Aust. J. Chem. 1981, 34, 927-932. d) den Hertog, H.J.; Schepman, F.R.; de Bruyn, J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1281-1288. 4-Pyridinol: e) Pfanz, H.; Dorn, H. Arch. Pharm. 1956, 289, 651-653.
3. 2-Pyridinol: a) Magidson, O.; Menshikoff, G. Ber. dtsch. chem. Ges. 1925, 58, 113-118. 3-Pyridinol: b) Koch, V.; Schnatterer, S. Synthesis 1990, 497-498. c) Clark,G.J.; Deady, L.W. Aust. J. Chem. 1981, 34, 927-932. d) den Hertog, H.J.; Schepman, F.R.; de Bruyn, J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1281-1288. 4-Pyridinol: e) Pfanz, H.; Dorn, H. Arch. Pharm. 1956, 289, 651-653.
4. 2-Pyridinol: a) Magidson, O.; Menshikoff, G. Ber. dtsch. chem. Ges. 1925, 58, 113-118. 3-Pyridinol: b) Koch, V.; Schnatterer, S. Synthesis 1990, 497-498. c) Clark,G.J.; Deady, L.W. Aust. J. Chem. 1981, 34, 927-932. d) den Hertog, H.J.; Schepman, F.R.; de Bruyn, J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1281-1288. 4-Pyridinol: e) Pfanz, H.; Dorn, H. Arch. Pharm. 1956, 289, 651-653.
5. 2-Pyridinol: a) Magidson, O.; Menshikoff, G. Ber. dtsch. chem. Ges. 1925, 58, 113-118. 3-Pyridinol: b) Koch, V.; Schnatterer, S. Synthesis 1990, 497-498. c) Clark,G.J.; Deady, L.W. Aust. J. Chem. 1981, 34, 927-932. d) den Hertog, H.J.; Schepman, F.R.; de Bruyn, J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1281-1288. 4-Pyridinol: e) Pfanz, H.; Dorn, H. Arch. Pharm. 1956, 289, 651-653.
6. 2-Pyridinol: a) Magidson, O.; Menshikoff, G. Ber. dtsch. chem. Ges. 1925, 58, 113-118. 3-Pyridinol: b) Koch, V.; Schnatterer, S. Synthesis 1990, 497-498. c) Clark,G.J.; Deady, L.W. Aust. J. Chem. 1981, 34, 927-932. d) den Hertog, H.J.; Schepman, F.R.; de Bruyn, J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1281-1288. 4-Pyridinol: e) Pfanz, H.; Dorn, H. Arch. Pharm. 1956, 289, 651-653.
7. 2-Pyridinol: a) Takahashi, T.; Yoneda, F. Chem. Pharm. Bull. 1958, 6, 611-614.
8. b) Broekman, F.W.; Tendeloo, H.J.C. Rec. Trav. Chim. Pays-Bas 1962, 81, 107-111.
9. 3-Pyridinol: c) Binz, A.; Maier-Bode, H. Angew. Chem. 1936, 49, 486-489.
10. d) von Schickh, O.; Binz, A.; Schulz, A. Ber. Chem. Ges. 1936, 69, 2593-2605.
11. e) Plazek, E.; Rodewald, Z. Roczniki Chem. 1936, 16, 502-508. See also the reference 3b 4-Pyridinol: see the reference 3b.
12. Iodination with ICl: a) Ochiai, E.; Fujimoto, Chem. Pharm. Bull. 1954, 2, 131-137.
13. Iodination with NaOCl/NaI: b) Edgar, K.J.; Falling, S.N. J. Org. Chem. 1990, 55, 5287-5291.
14. For example: a) Mariella, R.P.; Belcher, E.P. J. Am. Chem. Soc. 1952, 74, 1916-1919.
15. b) Bojarska-Dahling, H.; Nantka-Namirski, P. Roczniki Chem. 1953, 29, 1007-1018. See also: Binz, A.; Räth, C.; Maier-Bode, H. Ann. 1930, 478, 22-42.
16. b) Bojarska-Dahling, H.; Nantka-Namirski, P. Roczniki Chem. 1953, 29, 1007-1018. See also: Binz, A.; Räth, C.; Maier-Bode, H. Ann. 1930, 478, 22-42.
17. a) Kruger, S.; Mann, F.G. J. Chem. Soc. 1955, 2755-2763.
18. b) Berrie, A.H.; Newbold, G.T.; Spring, F.S. J. Chem. Soc. 1952, 2042-2046.
19. Brunel Y., Rousseau G. Tetrahedron Lett. 36:1995;8217-8221.
20. Reagent 1 was prepared as previously reported: Simonot, B.; Rousseau, G. J. Org. Chem. 1993, 58, 4-5. Reagent 2 was obtained using the same procedure.
21. 3) δ 12.0 (bs, 1H), 8.05 (d, J = 9.5 Hz, 1H), 7.95 (bs, 1H), 7.32 (d, J = 9.5 Hz, 1H), 6.0 (bs, 1H); mp: 243°C (sublimation).