New aspect of methanesulfonyl chloride: Unusual deoxygenations of pyridine N-oxides with methanesulfonyl chloride and triethylamine

Chemistry Letters

Volumn , Issue 8, 1998, Pages 829-830

  Morimoto, Yoshiki ^a   Kurihara, Hajime ^a   Yokoe, Chiho ^a   Kinoshita, Takamasa ^a  

^a Osaka City University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032327328     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.829     Document Type: Article

References (16)

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3. Y. Morimoto and C. Yokoc, Tetrahedron Lett., 38, 8981 (1997).
4. N. Fusetani, K. Yasumuro, S. Matsunaga, and H. Hirota, Tetrahedron Lett., 30, 6891 (1989).
5. +) 250.0082, found 250.0102.
6. a) R. A. Abramovitch and J. G. Saha, Adv. Heterocycl. Chem., 6, 229 (1966).
7. b) M. R. Grimmett, Adv. Heterocycl. Chem., 58, 271 (1993).
8. For example of the deoxygenation with chlorine-containing reagent without chlorination of the pyridine nucleus, see: c) A. Katritzky and C. W. Rees, "Comprehensive Heterocyclic Chemistry," Pergamon Press, Oxford (1984), Vol. 2, p. 261.
9. For the relevant deoxygenations of pyridine N-oxide derivatives employing sulfur-containing reagents, see: a) F. A. Daniher and B. E. Hackley, Jr., J. Org. Chem., 31, 4267 (1966).
10. b) B. F. Bonini, G. Maccagnani, G. Mazzanti, and P Pedrini, Tetrahedron Lett., 1979, 1799.
11. c) G. A. Olah, M. Arvanaghi, and Y. D. Vankar, Synthesis, 1980, 660.
12. D. J. R. Massy and A. McKillop, Synthesis, 1996, 1477.
13. For reviews on the chemistry of pyridine N-oxides, see: a) E. Ochiai, J. Org. Chem., 18, 534 (1953).
14. b) E. N. Shaw, Pyridine and Derivatives Part Two in "The Chemistry of Heterocyclic Compounds," ed by E. Klingsberg, Interscience Publishers, Inc., New York (1961), Chap. IV, p. 97.
15. The pyridine N-oxides 5, 9, 11, 13, and 15 except for the commercially available 7, 17, and 19 were prepared from the corresponding pyridine precursors via m-CPBA oxidation.
16. 2Cl, such a compound concerning the leaving moiety as manifested the reaction mechanism could not be caught.