Direct access to various 1-substituted-imidazo[1,5-a]pyridine-3(2H)-thione derivatives

Bulletin of the Korean Chemical Society

Volumn 28, Issue 4, 2007, Pages 685-688

  Kim, Ikyon ^a   Ge, Hyeoung Lee ^a   Zae, Sung No ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

1 Substituted (pyridin 2 yl) methylamines; 1 Substituted imidazo 1,5 a pyridine 3(2H) thione; N silylaldimines; Nucleophilic addition; Organometallic reagents

Indexed keywords

EID: 34247620673     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2007.28.4.685     Document Type: Article

References (25)

1. Glover, E. E.; Vaughan, K. D.; Bishop, D. C. J. Chem. Soc., Perkin Trans. 1 1973, 2595.
2. Recently, Movassaghi and Schmidt converted i to ii to measure the enantiomeric excess of the chiral imidazopyridinium derivatives they prepared. - Tetrahedron Lett. 2007, 48, 101. (Chemical Equation Presented)
3. Winthrop, S. O.; Gavin, G. J. Org. Chem. 1959, 24, 1936.
4. For the synthesis of phenyl 2-pyridyl ketone, see: (a) Niemers, E.; Hiltmann, R. Synthesis 1976, 593.
5. (b) Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1987, 52, 3901.
6. (c) Negi, S.; Matsukura, M.; Mizuno, M.; Miyake, K.; Minami, N. Synthesis 1996, 991.
7. (d) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238.
8. (e) Popova, I. S.; Formanovsky, A. A.; Mikhura, I. V. Russ. Chem. Bull., Int. Ed. 2002, 51, 540.
9. (f) Maerten, E.; Hassouna, F.; Couve-Bonnaire, S.; Mortreux, A.; Carpentier, J.-F.; Castanet, Y. Synlett 2003, 1874.
10. (g) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033.
11. (h) Yin, Z.; Zhang, Z.; Kadow, J. F.; Meanwell, N. A.; Wang, T. J. Org. Chem. 2004, 69, 1364.
12. (i) Hosseini Savari, M.; Sharghi, H. Synthesis 2004, 2165.
13. For recent reviews on nucleophilic addition to imines, see: (a) Vilaivan, T.; Bhanthumnavin, W.; Sritana-Anant, Y. Curr. Org. Chem. 2005, 9, 1315.
14. (b) Savoia, D. In Topics in Organometallic Chemistry; Lemaire, M.; Mangeney, P., Eds.; Springer: Berlin/ Heidelberg, 2005; Vol.15, pp 1-58.
15. (c) Petrini, M.; Torregiani, E. Synthesis 2007, 159.
16. (a) Hart, D. J.; Kanai, K.-i. J. Org. Chem. 1982, 47, 1555.
17. (b) Hart, D. J.; Kanai, K.-i.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289.
18. (c) Hart, D. J.; Hong, W.-P.; Hsu, L.-Y. J. Org. Chem. 1987, 52, 4665.
19. For nucleophilic addition of CN to N-TMS aldimines, see: Chu, G.-H.; Gu, M.; Gerard, B.; Dolle, R. E. Synth. Comm. 2004, 34, 4583. - Two substrates (2- and 3-pyridinealdehydes) examined in this reaction furnished the desired α-aminonitriles in low yield.
20. For example, competitive enolization of the aldehydes and/or isomerization of the imines to enamines might occur in case of enolizable aldehydes.
21. Since the stereochemistry at C1 is inconsequential in our case, we did not attempt to use any chiral ligands for asymmetric induction.
22. Bristol, J. A.; Lovey, R. G. U.S. Patent 4,419,516, 1982.
23. Presumably, halogen-metal exchange of methyl-substituted 2-bromopyridines competes with deprotonation of other position.
24. All new compounds exhibited satisfactory spectral and analytical data.
25. 3N in refluxing MeOH in most cases, no column chromatography was undertaken, which provided comparable overall yields.