One-step conversion of pyridine N-oxides to tetrazolo[1,5-a]pyridines

Journal of Organic Chemistry

Volumn 71, Issue 25, 2006, Pages 9540-9543

  Keith, John M ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN OXIDES; OPTIMIZATION; SCREENING; SOLVENTS; SULFONATION; THERMAL EFFECTS;

PHOSPHORYL AZIDES; PYRIDINES;

CHEMICAL MODIFICATION;

OXIDE; PYRIDINE DERIVATIVE; TETRAZOLE DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CYCLOADDITION; HEATING; QUANTUM YIELD; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 33845520080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061819j     Document Type: Article

References (42)

1. (a) Boruah, A.; Baruah, M.; Prajapati, D.; Sandhu, J. S. Synlett 1997, 1253-1254.
2. (b) Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24, 763-764.
3. (c) Boyer, J. H. J. Am. Chem. Soc. 1951, 73, 5865-5866.
4. (a) Tsao, M.-L.; Platz, M. S. J. Am. Chem. Soc. 2003, 125, 12014-12025.
5. (b) Murata, S.; Yoshidome, R.; Satoh, Y.; Kato, N.; Tomioka, H. J. Org. Chem. 1995, 60, 1428-1434.
6. (c) Albini, A.; Bettinetti, G.; Minoli, G. J. Am. Chem. Soc. 1991, 113, 6928-6934.
7. (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P. R.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057.
8. (b) Angell, Y.; Burgess, K. J. Org. Chem. 2005, 70, 9595-9598.
9. Brigas, A. F. Sci. Synth. 2004, 13, 861-915.
10. (a) Karvellas, C.; Williams, C. I.; Whitehead, M. A.; Jean-Claude, B. J. THEOCHEM 2001, 535 199-215.
11. (b) Kanyalkar, M.; Coutinho, E. C. Tetrahedron 2000, 56, 8775-8777.
12. (c) Cmoch, P.; Stefaniak, L.; Webb, G. A. Magn. Reson. Chem. 1997, 35, 237-242.
13. (d) Guimon, C.; Khayar, S.; Pfister-Guillouzo, G.; Claramunt, R. M.; Elguero, J. Spectrosc. Lett. 1981, 14, 747-753.
14. (e) Boyer, J. H.; Miller, E. J., Jr. J. Am. Chem. Soc. 1959, 81, 4671-4673.
15. (f) Denisov, A. Yu.; Krivopalov, V. P.; Mamatyuk, V. I.; Mamaev, V. P. Magn. Reson. Chem. 1988, 26, 42-46.
16. (a) Simoni, D.; Rondanin, R.; Furno, G.; Aiello, E.; Invidiata, F. P. Tet. Lett. 2000, 41, 2699-2703.
17. (b) Wentrup, C.; Winter, H. W. J. Am. Chem. Soc. 1980, 102, 6159-6161.
18. (a) Reisinger, A.; Koch, R.; Wentrup, C. J. Chem. Soc., Perkin Trans. 1 1998, 15, 2247-2250.
19. (b) Kuzaj, M.; Luerssen, H.; Wentrup, C. Angew. Chem. 1986, 98, 476-477.
20. Sasaki, T.; Kanematsu, K.; Murata, M. Tetrahedron 1971, 27, 5359-5366.
21. (a) Zhong, P.; Guo, S.-R. Chin. J. Chem. 2004, 22, 1183-1186.
22. (b) Rogers, R. B.; Gerwick, B. C.; Egli, E. A. US Pat. 4474599, 1984.
23. Boyer, J. H.; Chang, M. S.; Remisch, R. F. J. Org. Chem. 1960, 25, 286-287.
24. (a) Cmoch, P.; Wiench, J. W.; Stefaniak, L.; Sitkowski, J. J. Mol. Struct. 1999, 477, 119-125.
25. (b) Messmer, A.; Hajos, G.; Juhasz-Riedl, Z.; Sohar, P. J. Org. Chem. 1988, 53, 973-975.
26. Messmer, A.; Hajos, G.; Fleischer, J.; Czugler, M. Monatsh. Chem. 1985, 116, 1227-1231.
27. (a) Boyer, J. H.; Schoen, W. J. Am. Chem. Soc. 1956, 78, 423-425.
28. (b) Carboni, S.; Da Settimo, A.; Ferrarini, P. L.; Pirisino, G. Gazz. Chim. Ital. 1966, 96, 1456-1469.
29. (a) Seide, O. Ber. 1926, 59B, 2465-2473.
30. (b) Henecka, H. Ann. 1953, 583, 110-128.
31. Lee, C.-S.; Ohta, T.; Shudo, K.; Okamoto, T. Heterocycles 1981, 16, 1081-1084.
32. Boudakian, M. M.; Frulla, F. F.; Gavin, D. F.; Zaslowsky, J. A. J. Heterocycl. Chem. 1967, 4, 375-376.
33. Reddy, K. S.; Iyengar, D. S.; Bhalerao, U. T. Chem. Lett. 1983, 1745-1748.
34. Andrews, D. M.; Page, T. C. M.; Peach, J. M.; Pratt, A. J. J. Chem. Soc., Perkin Trans. 1 1995, 1045-1048.
35. Entries 1 and 3 showed small differences in yield; adding base to MsCl (entries 9 and 10) gave a tarry mixture containing some reduced product (see below).
36. 2Cl, like phenylmethanesulfonyl chloride, does not appear to require base to act as a reducing agent, possibly as a result of it more readily forming the sulfene. A small amount of reduced N-oxide was detected when MsCl was used as the activating group; see: Morimoto, Y.; Kurihara, H.; Shoji, T.; Kinoshita, T. Heterocycles 2000, 53, 1471-1474. (Chemical Equation Presented).
37. The heterogeneity of the reaction mixture may have been responsible for the low to nonexistent yields obtained with the nitrophenylsulfonyl chlorides.
38. Sulfuryl chloride (Table 1, entries 21 and 22) gave some desired product, but also a small amount (5 %) of the dehydratively coupled product (2), possibly arising via the mechanism shown below. Differentially functionalized bipyridyls could be very useful intermediates in the synthesis of metal ligands. We are presently pursuing the optimization of dehydratively coupling pyridine N-oxides. (Chemical Equation Presented).
39. 3 and a less electrophilic monoalkyl azidophosphate. Chlorodiphenylphosphine oxide formed a chromatographically stable azide, but it was unreactive under our standard conditions.
40. Though the sulfonyl halides gave comparable yields under some conditions, the products obtained from those reactions possessed trace amounts of color-imparting impurities making the products slightly yellow to orange as compared to bright white when DPPA was used.
41. Trapping the TMSCl generated in the reaction mixture was a concern, especially for large-scale preparations.
42. A reaction containing 4-nitropyridine N-oxide began to effervesce at 75°C, and heating was stopped for perceived potential safety reasons.