Regioselective synthesis of 5-alkylidene and 5-(iodoalkylidene)-pyrrol- 2(5H)-ones by halolactamisation of (2Z,4E)-dienamides and (Z)-alk-2-en-4- ynamides

Tetrahedron Letters

Volumn 45, Issue 10, 2004, Pages 2063-2066

  Cherry, Khalil ^a   Thibonnet, Jérôme ^a,b   Duchêne, Alain ^a   Parrain, Jean Luc ^b   Abarbri, Mohamed ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Halolactamisation; Pyrrolones

Indexed keywords

5 ALKYLIDENE; ALKADIENE; ALKYL GROUP; AMIDE; IODINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ALKYLATION; ARTICLE; ARYLATION; CYCLIZATION; HALOLACTAMISATION; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 1242318515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.063     Document Type: Article

References (48)

1. Celmer W.D., Solomons I.A. J. Am. Chem. Soc. 77:1955;2861.
2. Simmons C.J., Marner F.-J., Cardellina J.H. II, Moore R.E., Seff K. Tetrahedron Lett. 20:1979;2003.
3. Cardellina J.H. II, Moore R.E. Tetrahedron Lett. 20:1979;2007.
4. Abdullaev N.D., Samikov K., Antsupova T.P., Yagudaev M.R., Yunusov S.Yu. Khim. Prir. Soedin. (5):1987;692. [Chem. Nat. Compd. (Engl. Transl.), 1987, 23, 576].
5. Falk H., Grubmayr K., Herzig U., Hofer O. Tetrahedron Lett. 16:1975;559.
6. Lightner D.A., Park Y.-T. J. Heterocycl. Chem. 14:1977;415.
7. For recent synthesis see: Brückner R. Curr. Org. Chem. 5(6):2001;679.
8. Rossi R., Bellina F. Targets Heterocycl. Syst. 5:2001;169.
9. Brückner R. Chem. Commun. 2001;141.
10. Hanisch I., Brückner R. Synlett. 2000;374.
11. Brückner R., Ohe F.v.d. New J. Chem. 2000;659.
12. Siegel K., Brückner R. Synlett. 1999;1227.
13. Xu C., Negishi E.-I. Tetrahedron Lett. 40:1999;431.
14. Ma S., Shi Z. J. Org. Chem. 63:1998;6387.
15. Görth F.C., Umland A., Brückner R. Eur. J. Org. Chem. 1998;1055.
16. Rossi R., Bellina F., Biagetti M., Mannina L. Tetrahedron Lett. 39:1998;7799.
17. Rossi R., Bellina F., Biagetti M., Mannina L. Tetrahedron Lett. 39:1998;7599.
18. Rossi R., Bellina F., Mannina L. Tetrahedron Lett. 39:1998;3017.
19. Rossi R., Bellina F., Bechini C., Mannina L., Vergamini P. Tetrahedron. 54:1998;135.
20. Marshall J.A., Wolf M.A., Wallace E.M. J. Org. Chem. 62:1997;367.
21. Kotora M., Negishi E.-I. Synthesis. 1997;121;
22. Negishi E.-I., Kotora M. Tetrahedron. 53:1997;6707.
23. Marshall J.A., Wolf M.A. J. Org. Chem. 61:1996;3238.
24. Marshall J.A., Wallace E.M. J. Org. Chem. 60:1995;796.
25. Wuckelt J., Döring M., Langer P., Beckert R., Görls H. J. Org. Chem. 64:1999;365.
26. Yoshimatsu M., Machida K., Fuseya T., Shimizu H., Kataoka T. J. Chem. Soc., Perkins Trans. 1996;1839.
27. Abell A.D., Oldham M.D., Taylor J.M. J. Chem. Soc., Perkin Trans. 1. 1995;953.
28. Murakami M., Hayashi M., Ito Y. J. Org. Chem. 59:1994;7910.
29. Gill G.B., James G.D., Oates K.V., Pattenden G. J. Chem. Soc., Perkin Trans. 1. 23:1993;2567.
30. Fiorenza M., Reginato G., Ricci A., Taddei M. J. Org. Chem. 49:1984;551.
31. Walton H.M. J. Org. Chem. 22:1957;315.
32. Rousset S., Abarbri M., Thibonnet J., Duchêne A., Parrain J.-L. Chem. Commun. 2000;1987.
33. Cherry K., Abarbri M., Parrain J.-L., Duchêne A. Tetrahedron Lett. 44:2003;5791.
34. Abarbri M., Parrain J.-L., Kitamura M., Noyori R., Duchêne A. J. Org. Chem. 65:2000;7475.
35. Thibonnet J., Abarbri M., Duchêne A., Parrain J.-L. Synlett. 1999;141.
36. Thibonnet J., Abarbri M., Parrain J.-L., Duchêne A. Synlett. 1997;771.
37. Abarbri M., Parrain J.-L., Cintrat J.-C., Duchêne A. Synthesis. 1996;82.
38. Abarbri M., Parrain J.-L., Duchêne A. Tetrahedron Lett. 36:1995;2469.
39. Duchêne A., Abarbri M., Parrain J.-L., Kitamura M., Noyori R. Synlett. 1994;524.
40. Rousset S., Thibonnet J., Abarbri M., Duchêne A., Parrain J.-L. Synlett. 2000;260.
41. Abarbri M., Parrain J.-L., Duchêne A. Synth. Commun. 28:1998;239.
42. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467.
43. Sonogashira S. Stang P.J., Diederich F. Metal-Catalyzed Cross-Coupling Reactions. 1998;203 Wiley-VCH, Weinheim.
44. 2 and sp carbon centers. Vol. 3: 1991;521 Pergamon, Oxford.
45. 3, 50 MHz) δ (ppm): 19.5, 54.6, 74.2, 126.9, 127.2, 128.0 (2C), 128.6 (2C), 128.8 (2C), 129.3, 130.5 (2C), 140.4, 141.1, 146.1, 151.9, 157.6.
46. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457.
47. Suzuki A. J. Organomet. Chem. 576:1999;147.
48. 3, 200 MHz) δ (ppm): 1.55 (s, 3H), 2.44 (s, 3H), 4.73 (s, 2H), 6.34 (br s, 1H), 7.20-7.49 (m, 14H).