A straightforward synthesis of conhydrine by hetero Diels-Alder strategy mediated by microwaves

Tetrahedron Letters

Volumn 51, Issue 6, 2010, Pages 933-934

  Bandini, Elisa ^a   Corda, Giulia ^a   D'Aurizio, Antonio ^a   Panunzio, Mauro ^b  

^a CNR   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Azadiene; Conhydrine; Diels Alder; Microwaves

Indexed keywords

CONHYDRINE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; MICROWAVE RADIATION;

ALNUS;

EID: 73249129098     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.039     Document Type: Article

References (36)

1. Casiraghi G., Zanardi F., and Spanu P. Chem. Rev. 95 (1995) 1677-1716
2. Elbein A.D., and Molyneux R.J. Alkaloids: Chemical and Biological Perspective (1986), Wiley, New York
3. Reynolds T. Phytochemistry 66 (2005) 1399-1406
4. Mitchinson A., and Nadin A. J. Chem. Soc., Perkin Trans. 1 (1999) 2553-2581
5. Nadin A. J. Chem. Soc., Perkin Trans. 1 (1998) 3493-3513
6. Bailey P.D., Millwood P.A., and Smith P.D. J. Chem. Soc., Chem. Commun. (1998) 633-640
7. Laschat S., and Dickner T. Synthesis (2000) 1781-1813
8. Laschat S. Liebigs Ann. Chem. (1996) 1-11
9. Buffat M.G.P. Tetrahedron 60 (2004) 1701-1729
10. Zhu W., Mena M., Jnoff E., Sun N., Pasau P., and Ghosez L. Angew. Chem., Int. Ed. 48 (2009) 5880-5883
11. Panunzio M., and Vicennati P. In: Pandalai S.G. (Ed). Recent Research Development in Organic Chemistry Vol. 6 (2002), Transworld Research Network, Trivandrum, India 683-707
12. Burke A.J., Davies S.G., Garner A.C., McCarthy T.D., Roberts P.M., Smith A.D., Rodriguez-Solla H., and Vickers R.J. Org. Biomol. Chem. 2 (2004) 1387-1394
13. Agami C., Couty F., and Rabasso N. Tetrahedron Lett. 41 (2000) 4113
14. Chang M.-Y., Kung Y.-H., and Chen S.-T. Tetrahedron 62 (2006) 10843
15. Chang M.Y., Kung Y.H., and Chen S.T. Tetrahedron 62 (2006) 10843-10848
16. Enders D., Nolte B., Raabe G., and Runsink J. Tetrahedron: Asymmetry 13 (2002) 285-291
17. Guerreiro P., Ratovelomanana-Vidal V., and Genet J.P. Chirality 12 (2000) 408-410
18. Jamieson A.G., and Sutherland A. Org. Lett. 9 (2007) 1609-1611
19. Kandula S.R.V., and Kumar P. Tetrahedron: Asymmetry 16 (2005) 3268
20. Kandula S.V., and Kumar P. Tetrahedron Lett. 44 (2003) 1957
21. Lebrun S., Couture A., Deniau E., and Grandclaudon P. Tetrahedron: Asymmetry 19 (2008) 1245-1249
22. Lysenko I.L., Bekish A.V., and Kulinkovich O.G. Russ. J. Org. Chem. 38 (2002) 875-879
23. Masaki Y., Imaeda T., Nagata K., Oda H., and Ito A. Tetrahedron Lett. 30 (1989) 6395-6396
24. Nagata K., Toriizuka Y., and Itoh T. Heterocycles 66 (2005) 107-109
25. Pandey S.K., and Kumar P. Tetrahedron Lett. 46 (2005) 4091
26. Rodriguez D., Pico A., and Moyano A. Tetrahedron Lett. 49 (2008) 6866-6869
27. Roy S., Sharma A., Mula S., and Chattopadhyay S. Chem. Eur. J. 15 (2009) 1713-1722
28. Saikia P.P., BaiShya G., Goswami A., and Barua N.C. Tetrahedron Lett. 49 (2008) 6508-6511
29. Srivastava A.K., Das S.K., and Panda G. Tetrahedron 65 (2009) 5322-5327
30. Voituriez A., Ferreira F., and Chemla F. J. Org. Chem. 72 (2007) 5358-5361
31. For the synthesis of the azadiene 3, the starting aldehyde 1 was prepared, in optically active form, in 73% yield from commercially available α-hydroxy acid according:. Ahmed F., Al-Mutairi E.H., Avery K.L., Cullis P.M., Primrose W.U., Roberts G.C.K., and Willis C.L. Chem. Commun. (1999) 2049-2050
32. See also:. Moore G.C., Murphy P.J., Williams H.L., McGownb A.T., and Smith N.K. Tetrahedron 63 (2007) 11771-11780
33. De Lucchi O., and Pasquato L. Tetrahedron 44 (1988) 6755-6794
34. Kappe C.O., and Dallinger D. Mol. Divers. 13 (2009) 71-193
35. Moseley J.D. Chim. Oggi-Chem. Today 27 (2009) 6
36. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284