Synthesis of pyridine and isoquinoline derivatives by the palladium-catalyzed cyclization of olefinic ketone O-pentafluorobenzoyloximes

Chemistry Letters

Volumn , Issue 6, 2001, Pages 526-527

  Tsutsui, Hironori ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035533933     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.526     Document Type: Article

References (17)

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2. Recently, Uemura et al. have reported an example of oxidutive addition of cyclobutanone oximes to palladium(0) complex. T. Nishimura and S. Uemura, J. Am. Chem. Soc., 122, 12049 (2000).
3. 1 O-acetyl and O-benzoyloximes are not so reactive under the palladium-catalyzed cyclization conditions. For example, it takes 10 h to consume the O-benzoyl analogue and the pyrrole is obtained in 35% yield, though the cyclization of O-pentafluorobenzoyloxime is complete only 1 h to give the pyrrole in 86% yield.
4. 1 and 2a was decomposed.
5. It has been known that the addition of quaternary ammonium halides causes dramatic influence on the reactivity of the Heck reaction, see: B. C. Soderberg. "Transition Metal Alkyl Complexes: Oxidative Addition and Insertion," in "Comprehensive Organometallic Chemistry II," ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford (1995), Vol. 12, Chap. 3.5, p. 259: S. Bräse and A. de Meijere, "Palladium-Catalyzed Coupling of Organyl Halides to Alkenes - The Heck Reaction." in "Metal-Catalyzed Cross Coupling Reactions," ed. by P. J. Stang and F. Diederich, John Wiley & Sons, New York (1998), and references cited therein.
6. It has been known that the addition of quaternary ammonium halides causes dramatic influence on the reactivity of the Heck reaction, see: B. C. Soderberg. "Transition Metal Alkyl Complexes: Oxidative Addition and Insertion," in "Comprehensive Organometallic Chemistry II," ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford (1995), Vol. 12, Chap. 3.5, p. 259: S. Bräse and A. de Meijere, "Palladium-Catalyzed Coupling of Organyl Halides to Alkenes - The Heck Reaction." in "Metal-Catalyzed Cross Coupling Reactions," ed. by P. J. Stang and F. Diederich, John Wiley & Sons, New York (1998), and references cited therein.
7. Palladium-mediated and -catalyzed pyridine, quinoline, and isoquinoline syntheses, see: a) T. Hosokawa, N. Shimo, K. Maeda, A. Sonoda, and S.-I. Murahashi, Tetrahedron Lett., 1976, 383.
8. L. S. Hegedus, G. F. Allen, J. J. Bozell, and E. L. Waterman. J. Am. Chem. Soc., 100, 5800 (1978).
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11. 1H NMR spectrum of the crude products from 1d, 2d did not isomerize to 2-benzyl-3-methoxy-5-phenylpyrrole (4d) with pyrrolidine.
12. 4NCl and triethylamine in DMF at 80 °C.
13. T. Mukaiyama, Org. React., 28, 203 (1982); T. Mukaiyama, S. Kobayashi, and M. Murakami, Chem. Lett., 1984, 1759.
14. T. Mukaiyama, Org. React., 28, 203 (1982); T. Mukaiyama, S. Kobayashi, and M. Murakami, Chem. Lett., 1984, 1759.
15. N. M. Kablaoui, F. A. Hicks, and S. L. Buchwald, J. Am. Chem. Soc., 119, 4424 (1997).
16. The oxime 9a was easily prepared by the reaction of o-allylacetophenone and hydroxylamine hydrochloride and pyridine, and successively reacted with pentafluorobenzoyl chloride and triethylamine.
17. 4.