DABCO-induced [2+2+2]-cycloaddition reaction of ethyl propiolate and aryl aldehydes for the synthesis of 4-aryl-4 H -pyrans

Synlett

Volumn , Issue 20, 2009, Pages 3295-3298

  Liu, Weibing ^a   Jiang, Huanfeng ^a   Zhou, Peng ^a   Zhu, Shifa ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

4 aryl 4 H pyrans; 2+2+2 cycloaddition reaction; Aldehydes; DABCO; Ethyl propiolate

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ALDEHYDE DERIVATIVE; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 72249114714     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218367     Document Type: Article

References (47)

1. Walji A M., MacMillan D W. C., Synlett 2007 1477
2. Tietze L F., Haunert F, Stimulating Concepts in Chemistry Wiley New York 2000
3. Wender P A., Miller B L., In Organic Synthesis: Theory and Applications Vol. 2, Hudlicky T, JAI Press Greenwich CT 1993 27
4. Müller T J. J., Metal Catalyzed Cascade Reactions, In Topics in Organometallic Chemistry Vol. 19 Springer New York 2006
5. Hayashi T, Yamasaki K, Chem. Rev. 2003 103 2829
6. Naodovic M, Yamamoto H, Chem. Rev. 2008 108 3132
7. Paull D H., Abraham C J., Scerba M T., Alden D E., Lectka T, Acc. Chem. Res. 2008 41 655
8. Terao J, Kambe N, Acc. Chem. Res. 2008 41 1545
9. Patil N T., Yamamoto Y, Chem. Rev. 2008 108 3395
10. Enders D, Grondal C, Huttl M R. M., Angew. Chem. Int. Ed. 2007 46 1570
11. Johnson A W., Tebby J C., J. Chem. Soc. 1961 2126
12. Tebby J C., Wilson I F., Grifiths D V., J. Chem. Soc., Perkin Trans. 1 1979 2133
13. Diels O, Alder K, Liebigs Ann. Chem. 1932 498 16
14. Acheson R M., Adv. Heterocycl. Chem. 1963 1 125
15. Yu X Z., Ren H J., Xiao Y J., Zhang J L., Chem. Eur. J. 2008 14 8481
16. Zhu S, Hudson T H., Kyle D E., Lin A J., J. Med. Chem. 2002 45 3491
17. Chung Y M., Gong J H., Kim T H., Kim J N., Tetrahedron Lett. 2001 42 9023
18. Ciclosi M, Fava C, Galeazzi R, Orena M, Sepulveda-Arques J, Tetrahedron Lett. 2002 43 2199
19. Kim J N., Lee H J., Lee K Y., Gong J H., Synlett 2002 173
20. Gong J H., Kim H R., Ryu E K., Kim J N., Bull. Korean Chem. Soc. 2002 23 789
21. Lawrence N J., Crump J P., McGown A T., Hadfield J A., Tetrahedron Lett. 2001 42 3939
22. Yadav J S., SubbaReddy B V., Geetha V, Synlett 2002 513
23. Wang B, Yu X.-M, Lin G.-Q, Synlett 2001 904
24. Rose P M., Clifford A A., Rayner C M., Chem. Commun. 2002 968
25. Gawronski J, Wascinska N, Gajewy J, Chem. Rev. 2008 108 5227
26. Brandi A, Cicchi S, Cordero F M., Chem. Rev. 2008 108 3988
27. Meng X T., Huang Y, Chen R Y., Org. Lett. 2009 11 137
28. Gonzalez R, Martin N, Seoane C, Tetrahedron Lett. 1992 33 3809
29. Shestopalov A M., Niazimbetova [nl]D H., Heterocycles 1999 51 1101
30. Mulwad V V., Shirodkar J M., Indian J. Heterocycl. Chem. 2002 11 199
31. Mulwad V V., Pawar R B., Indian J. Heterocycl. Chem. 2001 10 241
32. Lei Y J., Yang Y Z., Liu H, Zhu C H., Chin. J. Med. Chem. 2001 11 270
33. Kortenska V D., Velikova M P., Yanishlieva N V., Totzeva I R., Bankova V S., Marcucci M C., Eur. J. Lipid. Sci. Technol. 2002 104 19
34. Longobardi M, Mariani E, Bargagna A, Mazzeo F, Vitelli M R., Giordano L, Falcone G, Farmaco 2001 56 625
35. Horino H, Mimura T, Kagechika K, Ohta M, Kubo H, Kitagawa M, Chem. Pharm. Bull. 1998 46 602
36. Manolov L, Danchev N D., Arch. Pharm. 2003 336 83
37. Shafae A M., Ibrahim M A., Pharmazie 2003 58 143
38. Wu J Y., Fong W F., Zhang J X., Leung C H., Kwong H L., Meng S, Li D, Chenug H Y., Eur. J. Pharm. 2003 473 9
39. Yong J, Zhao Y F., Still C C., Sacalis J N., Tsinghua Sci. Technol. 2000 5 159
40. Ahluwalia V K., Kaila N, Bala S, Indian. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1987 26 700
41. Mail R S., Joshi P P., Sandhu P K., Manekar-Tilve A, J. Chem. Soc., Perkin Trans. 1 2002 371
42. Magiatis P, Melliou E, Skaltsounis A L., Mitaku S, Leonce S, Reard P, Pierre A, Atassi G, J. Nat. Prod. 1998 61 982
43. Madkour H M. F., Mahmoud M R., Sakr A M., Habashy M M., Sci. Pharm. 2001 69 33
44. Jolivet C, Rivalle C, Bisagni E, Heterocycles 1996 43 995
45. Marco J L., Delos R C., Carreiras M C., Banos J E., Badia A, Vivas N M., Bioorg. Med. Chem. 2001 9 727
46. Bloxhem J, Dell C P., Smith C W., Heterocycles 1994 38 399
47. Nair V, Sreekanth A R., Vinod A U., Org. Lett. 2001 3 3495