A novel oxidation-ring-contraction of Hantzsch 1,4-dihydropyridines to polysubstituted furans

Tetrahedron Letters

Volumn 48, Issue 30, 2007, Pages 5321-5324

  Liu, Zhengang ^a   Yu, Wei ^a   Yang, Li ^a   Liu, Zhong Li ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Hantzsch 1,4 dihydropyridines; Oxone; Polysubstituted furans

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; FURAN DERIVATIVE; SODIUM PEROXIDE;

ARTICLE; OXIDATION; PH; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

EID: 34250816221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.071     Document Type: Article

References (30)

1. Eisner U., and Kuthan J. Chem. Rev. 72 (1972) 1
2. Stout D.M., and Meyers A.I. Chem. Rev. 82 (1982) 223
3. Chennot T., and Eisner U. J. Chem. Soc., Perkin Trans. 1 (1975) 926
4. Pfister J.R. Synthesis (1990) 689
5. Vanden Eynde J.-J., D'Orazio R., and Van Haverbeke Y. Tetrahedron 50 (1994) 2479
6. Mashraqui S.H., and Karnik M.A. Tetrahedron Lett. 39 (1998) 4895
7. Yadav J.S., Subba Reddy B.V., Sabitha G., and Kiran Kumar Reddy G.S. Synthesis (2000) 1532
8. Zhu X.-Q., Zhao B.-J., and Cheng J.P. J. Org. Chem. 65 (2000) 8158
9. Nakamichi N., Kawashita Y., and Hayashi M. Org. Lett. 4 (2002) 3955
10. Arguello J., Nunez-Vergara L.J., Sturm J.C., and Squella J.A. Electrochim. Acta 49 (2004) 4849
11. Heravi M.M., Behbahani F.K., Oskooie H.A., and Shoar R.H. Tetrahedron Lett. 46 (2005) 2775
12. Jin M.-Z., Yang L., Wu L.-M., Liu Y.-C., and Liu Z.-L. Chem. Commun. (1998) 2451
13. Han B., Liu Q., Liu Z., Mu R., Zhang W., Liu Z.-L., and Yu W. Synlett (2005) 2333
14. Han B., Liu Z., Liu Q., Yang L., Liu Z.-L., and Yu W. Tetrahedron 62 (2006) 2492
15. Adam W., and Saha-Moller C.R. Org. React. 61 (2002) 219-516
16. Travis B.R., Narayan R.S., and Borhan B. J. Am. Chem. Soc. 124 (2002) 3824
17. Bloch B., Abecassis J., and Hassan D. J. Org. Chem. 50 (1985) 1544
18. Webster F.X., Rivas-Enterrios J., and Silverstein R.M. J. Org. Chem. 52 (1987) 689
19. Travis B., and Borhan B. Tetrahedron Lett. 42 (2001) 7741
20. Keay B.A., and Dibble P.W. In: Bird C.W. (Ed). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Elsevier, New York 395-436
21. Lipshutz B.H. Chem. Rev. 86 (1986) 795
22. Katritsky A.R. Advances in Heterocyclic Chemistry (1982), Academic Press, New York
23. Katritzky A.R., and Rees C.W. Comprehensive Heterocyclic Chemistry (1984), Pergamon, New York
24. Hou X.L., Cheung H.Y., Hon T.Y., Kwan P.L., Lo T.H., Tong S.Y., and Wong H.N.C. Tetrahedron 54 (1998) 1955 and references cited therein
25. Keay B.A. Chem. Soc. Rev. 28 (1999) 209 and references cited therein
26. For recent examples, see:. Yao T.-L., Zhang X.-X., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 11164
27. Jung C.-K., Wang J.-C., and Krische M.J. J. Am. Chem. Soc. 126 (2004) 4118
28. Liu Y.-H., Song F.-J., Song Z.-Q., Liu M.-N., and Yang B. Org. Lett. 7 (2005) 5409
29. 3, and then extracted with ethyl acetate (3 × 10 mL). The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under a reduced pressure. Products 2 and 3 were isolated from the residue by silica gel column chromatography (petroleum/acetone 15:1 to 10:1).
30. Li W., and Fuches P.L. Org. Lett. 5 (2003) 2853