Regioselective construction of polysubstituted pyridine ring from Baylis-Hillman adducts via sequential introduction of tosylamide, Michael reaction, aldol condensation, and elimination of TsH

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8799-8803

  Park, Da Yeon ^a   Lee, Mi Jung ^a   Kim, Taek Hyeon ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Baylis Hillman adducts; Cyclization; Michael reaction; Pyridines

Indexed keywords

4 TOLUENESULFINIC ACID; PYRIDINE; PYRIDINE DERIVATIVE; SULFINIC ACID DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BAYLIS HILLMAN REACTION; ISOMERIZATION; MICHAEL ADDITION;

EID: 27744478089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.034     Document Type: Article

References (24)

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12. M. Pal, V.R. Batchu, I. Dager, N.K. Swamy, and S. Padakanti J. Org. Chem. 70 2005 2376 and further references cited therein
13. For our recent publications on the chemical transformations of Baylis-Hillman adducts, see: S. Gowrisankar, K.Y. Lee, and J.N. Kim Tetrahedron Lett. 46 2005 4859
14. K.Y. Lee, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 46 2005 5387
15. C.G. Lee, K.Y. Lee, S. Lee, and J.N. Kim Tetrahedron 61 2005 1493 and further references cited therein
16. 3 in aq THF under refluxing conditions according to the previous paper. J.N. Kim, Y.M. Chung, and Y.J. Im Tetrahedron Lett. 43 2002 6209
17. J.N. Kim, H.J. Lee, K.Y. Lee, and H.S. Kim Tetrahedron Lett. 42 2001 3737
18. 3, 75 MHz): δ 25.58, 39.52, 39.58, 128.89, 129.45, 129.85, 133.72, 135.96, 144.51, 200.31.
19. For the applications of aldol type condensation reaction in the transformations of Baylis-Hillman adducts, see: J.N. Kim, J.M. Kim, and K.Y. Lee Synlett 2003 821
20. Y.J. Im, C.G. Lee, H.R. Kim, and J.N. Kim Tetrahedron Lett. 44 2003 2987
21. J.N. Kim, Y.J. Im, and J.M. Kim Tetrahedron Lett. 43 2002 6597
22. 3, 75 MHz): δ 21.55, 22.52, 32.50, 44.83, 45.34, 58.42, 73.33, 124.66, 127.33, 127.68, 128.54, 128.84, 129.83, 132.96, 135.93, 138.59, 143.93, 208.78. However, we did not determine the stereochemistry of this major component.
23. 3, 300 MHz): δ 1.69 (d, J = 6.9 Hz, 3H), 2.19 (s, 3H), 2.42 (s, 3H), 2.92 (dd, J = 12.0 and 5.1 Hz, 1H), 3.49 (dd, J = 13.5 and 2.1 Hz, 1H), 3.60 (t, J = 4.2 Hz, 1H), 4.03 (dd, J = 12.0 and 3.3 Hz, 1H), 4.46 (d, J = 13.5 Hz, 1H), 5.95 (q, J = 6.9 Hz, 1H), 6.65 (s, 1H), 7.13-7.63
24. 3, 75 MHz): δ 16.29, 36.78, 52.18, 126.47, 126.86, 128.37, 128.65, 135.31, 138.62, 147.62, 149.71, 153.26, 167.12.