2,3-Pyridyne formation by fluoride induced desilylation-elimination

Synthetic Communications

Volumn 27, Issue 20, 1997, Pages 3573-3579

  Walters, Michael A ^a   Shay, John J ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030756728     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708007079     Document Type: Article

References (21)

1. For leading references on the preparation of more highly-substituted 2,3-pyridynes and other arynes and hetarynes see: Reinecke, M. G. Tetrahedron 1982, 38, 427-498. van der Plas, H. C.; Roeterdink, F. In The Chemistry of Triple-bonded Functional groups Supplement C; S. Patai and Z. Rappoport, Ed.; John Wiley & Sons: Chichester, NY, 1983; pp 421-511. Hart, H. In Supplement C2;The Chemistry of Triple-bonded Functional Groups; S. Patai, Ed.; John Wiley & Sons: Chichester, 1994; Vol. 2; pp 1017-1134.
2. For leading references on the preparation of more highly-substituted 2,3-pyridynes and other arynes and hetarynes see: Reinecke, M. G. Tetrahedron 1982, 38, 427-498. van der Plas, H. C.; Roeterdink, F. In The Chemistry of Triple-bonded Functional groups Supplement C; S. Patai and Z. Rappoport, Ed.; John Wiley & Sons: Chichester, NY, 1983; pp 421-511. Hart, H. In Supplement C2;The Chemistry of Triple-bonded Functional Groups; S. Patai, Ed.; John Wiley & Sons: Chichester, 1994; Vol. 2; pp 1017-1134.
3. For leading references on the preparation of more highly-substituted 2,3-pyridynes and other arynes and hetarynes see: Reinecke, M. G. Tetrahedron 1982, 38, 427-498. van der Plas, H. C.; Roeterdink, F. In The Chemistry of Triple-bonded Functional groups Supplement C; S. Patai and Z. Rappoport, Ed.; John Wiley & Sons: Chichester, NY, 1983; pp 421-511. Hart, H. In Supplement C2;The Chemistry of Triple-bonded Functional Groups; S. Patai, Ed.; John Wiley & Sons: Chichester, 1994; Vol. 2; pp 1017-1134.
4. Fleet, G. W. J.; Fleming, I. J. Chem. Soc. (C) 1969, 1758-1763. Kurita, J.; Kakusawa, N.; Yasuike, S.; Tsuchiya, T. Heterocycles 1990, 31, 1937-1940.
5. Fleet, G. W. J.; Fleming, I. J. Chem. Soc. (C) 1969, 1758-1763. Kurita, J.; Kakusawa, N.; Yasuike, S.; Tsuchiya, T. Heterocycles 1990, 31, 1937-1940.
6. Mallet, M.; Queguiner, G.; Pastour, P. Comp. Rend. 1972, 274, 719-722. Cook, J. D.; Wakefield, B. J. J. Chem. Soc. (C) 1969, 1973-1978.
7. Mallet, M.; Queguiner, G.; Pastour, P. Comp. Rend. 1972, 274, 719-722. Cook, J. D.; Wakefield, B. J. J. Chem. Soc. (C) 1969, 1973-1978.
8. Martens, R. J.; den Hertog, H. J. Tetrahedron Lett. 1962, 643-645. Martens, R. J.; den Hertog, H. J. Rec. Trav. Chim. Pays-Bas 1964, 83, 621-630.
9. Martens, R. J.; den Hertog, H. J. Tetrahedron Lett. 1962, 643-645. Martens, R. J.; den Hertog, H. J. Rec. Trav. Chim. Pays-Bas 1964, 83, 621-630.
10. Walters, M. A.; Shay, J. J. Tetrahedron Lett. 1995, 36, 7575-7578.
11. Tsukazaki, M.; Snieckus, V. Heterocycles 1992, 33, 533-536.
12. a. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chemistry Lett. 1983, 1211-1214,
13. b. Shankaran, K.; Snieckus, V. Tetrahedron Lett. 1984, 25, 2827-2830.
14. Effenberger, F.; Daub, W. Chem. Ber. 1991, 124, 2119-2125.
15. Purchased from Aldrich.
16. Following the procedure of Stang: Stang, P. J.; Fisk, T. E. Synthesis 1979, 438-440.
17. All yields are unoptimized. The cycloaddition reactions gave no other identifiable products other than the anticipated cycloadducts. Apparently, 2,3-pyridyne is much more prone to polymerization than benzyne since reactions involving the latter intermediate usually proceeding in much higher yield. The analytical data for compounds 6, 7, 8, 9, and 11 was identical to that which has been reported previously in the literature.
18. Mallet, M.; Queguiner, G.; Pastour, P. Comp. Rend. 1972, 274, 719-722.
19. This compound has been prepared previously by another method: Warner, V. D.; Musto, J. D.; Turesky, S. S.; Soloway, B. J. Pharm. Sci. 1975, 64, 1563-1566.
20. 5 of 10 and in the related adducts formed from the reaction of substituted benzynes with 2-methoxyfuran. Giles, R. G. F.; Sargent, M. V.; Sianipar, H. J. Chem. Soc. Perkin Trans. 1 1991, 1571-1579.
21. Recent theoretical studies have found that 2,3-pyridyne is less stable than 3,4-pyridyne by 3.2 (BLYP/6-31G*) and 6.0 (B3LYP/6-31G*) kcal/mol. Liu, R.; Tate, D. R.; Clark, J. A.; Moody, P. R.; Van Buren, A. S.; Krauser, J. A. J. Phys. Chem. 1996, 700, 3430-3434.