Application of microwaves in organic synthesis: A rapid and efficient synthesis of new 3-aryl-2-imino-4-methyl-2,5-dihydrofurans and 3-aryl-3-2-(5H)-furanones

Synthetic Communications

Volumn 33, Issue 9, 2003, Pages 1575-1585

  Villemin, Didier ^a,c   Liao, Liang ^a,b  

^a UNIVERSITÉ DE CAEN   (France)

^b CLARK ATLANTA UNIVERSITY   (United States)

^c 6 Bd du Maréchal Juin   (France)

Author keywords

Iminolactone; Lactone; Microwave

Indexed keywords

2 IMINO 4 METHYL 2,5 DIHYDROFURAN DERIVATIVE; 2(5H) FURANONE DERIVATIVE; 4 METHYL 2(5H) FURANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; MICROWAVE RADIATION; PHOTOCHEMISTRY; POLYMERIZATION;

EID: 0038304195     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120018778     Document Type: Article

References (37)

1. For reviews on 2(5H)-furanones(but-2-en-4-olides) see: (a) Rao, Y.S. Chem. Rev. 1964, 64, 353;
2. (b) Rao, Y.S. Chem. Rev. 1976, 76, 625;
3. (c) Avetisyan A.A.; Dangyan, M.T. Russ. Chem. Rev. 1977, 46, 643;
4. (d) Knight, D.W. Contemporary Organic Synthesis 1994, 1, 287;
5. (e) Laduwahetty, T. Contemporary Organic Synthesis 1995, 2, 133;
6. (f) Collins, I. Contemporary Organic Synthesis 1996, 3, 295.
7. (a) Rupprecht, J.K.; Hui, Y.-H.; McLaughlin, J.L. J. Nat. Prod. 1990, 53, 237;
8. (b) Fang, X.; Rieser, M.J.; Gu, Z.M.; McLaughlin, J.L. Phytochem. Anal. 1993, 4, 27;
9. (c) Gu, Z.M.; Zhao, G.X.; Oberlies, N.H., Zeng, L.; McLaughlin, J.L. In Recent Advances in Phytochemistry; Arnason, J.T., Mata, R., Romeo, J.R., Eds.; Plenum Press: New York, 1995, Vol. 29, 249-310;
10. (d) Zeng, L.; Ye, Q.; Oberlies, G.; Shi, N.H.; Gu, Z.M.; He, K.; McLaughlin, J.L. J. Nat. Prod. Rep. 1996, 13, 275.
11. Marshallin, P.G. In: Chemistry of Carbon Compounds; Rodd, E.H., Ed.; Elsevier: New York, 1970; Vol. IID, Chapter 17.
12. Cavallito, C.J. Medicinal Chemistry; Suter, C.M., Ed.; Willey: New York, 1951, Vol. I, 221; Nineham, A.W.; Raphael, R.A. J. Chem. Soc. 1949, 118.
13. Cavallito, C.J. Medicinal Chemistry; Suter, C.M., Ed.; Willey: New York, 1951, Vol. I, 221; Nineham, A.W.; Raphael, R.A. J. Chem. Soc. 1949, 118.
14. Siddall, J.B. US Patent 3700694, 1972; Chem. Abstr. 1973, 78, 43254.
15. Siddall, J.B. US Patent 3700694, 1972; Chem. Abstr. 1973, 78, 43254.
16. Restock, T.L.; Sell, H.M. J. Am. Chem. Soc. 1952, 74, 274.
17. Payne, G.B. US Patent 3177227, 1965; Chem. Abstr. 1965, 63, 6866e.
18. Payne, G.B. US Patent 3177227, 1965; Chem. Abstr. 1965, 63, 6866e.
19. Fillol, L.; Miranda, M.A.; Morera, I.M.; Sheikh, H. Heterocycles 1990, 31, 751; Chem. Abst. 1990, 113, 58135r.
20. Fillol, L.; Miranda, M.A.; Morera, I.M.; Sheikh, H. Heterocycles 1990, 31, 751; Chem. Abst. 1990, 113, 58135r.
21. Villemin, D.; Liao, L. Tetrahedron Lett. 1996, 37, 8733; Villemin, D.; Jaffrès, P.-A.; Hachémi, M. Tetrahedron Lett. 1997, 38, 537; Villemin, D.; Hachemi, M. React. Kin. Cat. Lett. 2001, 72, 3.
22. Villemin, D.; Liao, L. Tetrahedron Lett. 1996, 37, 8733; Villemin, D.; Jaffrès, P.-A.; Hachémi, M. Tetrahedron Lett. 1997, 38, 537; Villemin, D.; Hachemi, M. React. Kin. Cat. Lett. 2001, 72, 3.
23. Villemin, D.; Liao, L. Tetrahedron Lett. 1996, 37, 8733; Villemin, D.; Jaffrès, P.-A.; Hachémi, M. Tetrahedron Lett. 1997, 38, 537; Villemin, D.; Hachemi, M. React. Kin. Cat. Lett. 2001, 72, 3.
24. For a review on focused microwave action: Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; For a general review on microwave activation: Kingston, H.M.; Haswell, S.J. Microwave-Enhanced Chemistry; American Chemical Society Publication, Columbus, USA, 1997.
25. For a review on focused microwave action: Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; For a general review on microwave activation: Kingston, H.M.; Haswell, S.J. Microwave-Enhanced Chemistry; American Chemical Society Publication, Columbus, USA, 1997.
26. Liao, L.; Villemin, D. J. Chem. Res. (C) 2000, 179 and references cited.
27. [13] but whatever the conditions we have obtain only iminolactone.
28. Melikian, G.; Rouessac, F.; Alexandre, C. Synth. Commun. 1993, 23, 2631.
29. (a) Vogel, P. Chimie Organique; DeBoech Université: Bruxelles, Belgique, 1997, 254 pp;
30. (b) Ingold, C.K. J. Chem. Soc. 1921, 305;
31. (c) Jung, M.E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224.
32. Mhiri, C.; Ladhar, F.; Le Bigot, Y.; El Gharbi, R. Synth. Commun. 1999, 29, 1451; Mhiri, C.; Le Bigot, Y.; El Gharbi, R. Synth. Commun. 1999, 29, 3385.
33. Mhiri, C.; Ladhar, F.; Le Bigot, Y.; El Gharbi, R. Synth. Commun. 1999, 29, 1451; Mhiri, C.; Le Bigot, Y.; El Gharbi, R. Synth. Commun. 1999, 29, 3385.
34. (a) Mangasaryan, Ts.A.; Matsoyan, S.G.; Dangyan, M.T.; Tatevosyan, G.E. Zhur. Org. Khim. 1972, 8, 876; Chem. Abstr. 1972, 77, 19460m;
35. (a) Mangasaryan, Ts.A.; Matsoyan, S.G.; Dangyan, M.T.; Tatevosyan, G.E. Zhur. Org. Khim. 1972, 8, 876; Chem. Abstr. 1972, 77, 19460m;
36. (b) Avetisyan, A.A.; Dzhandzhapanyan, A.N.; Bayatyan, B.E.; Dangyan, M.T. Arm. Khim. Zhur. 1975, 28, 819; Chem. Abstr. 1976, 84, 164110w.
37. (b) Avetisyan, A.A.; Dzhandzhapanyan, A.N.; Bayatyan, B.E.; Dangyan, M.T. Arm. Khim. Zhur. 1975, 28, 819; Chem. Abstr. 1976, 84, 164110w.