α-Iodination of enaminones with bis(pyridine)iodonium(I) tetrafluoroborate

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8397-8400

  Campos, Pedro J ^a   Arranz, Joaquín ^a   Rodríguez, Miguel A ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHENYLIODONIUM SALT; ENAMINE; HETEROCYCLIC COMPOUND; PHENAZONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; IODINATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY;

EID: 0030670185     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10231-3     Document Type: Article

References (11)

1. (a) Kordik, C. P.; Reitz, A. B. J. Org. Chem. 1996, 61, 5644.
2. (b) Matsuo, K.; Ishida, S.; Takuno, Y. Chem. Pharm. Bull. 1994, 42, 1149.
3. Hebernehl, G. G.; Wippermann, I.; Krebs, H. C.; Dieck, S. t. Z. Naturforsch. 1991, 46b, 1415. Jirkovsky, I. Can. J. Chem. 1974, 52, 55.
4. Hebernehl, G. G.; Wippermann, I.; Krebs, H. C.; Dieck, S. t. Z. Naturforsch. 1991, 46b, 1415. Jirkovsky, I. Can. J. Chem. 1974, 52, 55.
5. See, for example: Barluenga, J.; Gonzalez, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; Rodriguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567. Barluenga, J.; Gonzalez, J. M.; García-Martín, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
6. See, for example: Barluenga, J.; Gonzalez, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; Rodriguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567. Barluenga, J.; Gonzalez, J. M.; García-Martín, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
7. See, for example: Barluenga, J.; Gonzalez, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; Rodriguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567. Barluenga, J.; Gonzalez, J. M.; García-Martín, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
8. Campos, P. J.; Tan, C-Q.; Rodríguez, M. A. Tetrahedron Lett. 1995, 36, 5257.
9. Gramain, J.-C.; Husson, H.-P.; Troin, Y. J. Org. Chem. 1985, 50, 5517.
10. 7 (1 mmol). After stirring for two hours, the solution was filtered, washed with sodium bicarbonate solution, and extracted with methylene chloride. The organic phase was dried over anhydrous sodium sulphate. Removal of solvents in vacuo gave the corresponding α-iodo enaminone as a solid which was essentially pure (g.c. purity > 95 %).
11. Enaminones 1a-Ic and 3a-3c were synthesized as described in reference 5. 1d and 5 were purchased from Aldrich Chemical Company.