Efficient microwave-assisted formation of functionalized 2,5-dihydropyrroles using ruthenium-catalyzed ring-closing metathesis

Tetrahedron Letters

Volumn 45, Issue 15, 2004, Pages 3089-3092

  Balan, Daniela ^a   Adolfsson, Hans ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

2,5 Dihydropyrroles; Aza Baylis Hillman reaction; Microwave assisted synthesis; Ring closing metathesis

Indexed keywords

ALKADIENE; PYRROLE DERIVATIVE; RUTHENIUM;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; MICROWAVE RADIATION; REACTION ANALYSIS; RING CLOSING METATHESIS; TECHNIQUE;

EID: 1642373105     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.100     Document Type: Article

References (27)

1. For recent reviews on olefin metathesis, see: Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
2. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012-3043.
3. Schwab P., Grubbs R.H., Ziller J.W. J. Am. Chem. Soc. 118:1996;100-110.
4. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953-956.
5. For recent examples on the formation of heterocyclic compounds using RCM, see: Walters M.A. Gribble G., Joule J.A. Progress in Heterocyclic Chemistry. 15:2003;1-36 Pergamon, Oxford.
6. For recent examples, see: Zaja M., Connon S.J., Dune A.M., Rivard M., Buschmann N., Jiricek J., Blechert S. Tetrahedron. 59:2003;6454-6558.
7. Fürstner A., Thiel O.R., Ackermann L., Schanz H.-J., Nolan S.P. J. Org. Chem. 65:2000;2204-2207.
8. Grigg R., Martin W., Morris J., Sridharan V. Tetrahedron Lett. 44:2003;4899-4901.
9. Grigg R., Hodgeson A., Morris J., Sridharan V. Tetrahedron Lett. 44:2003;1023-1026.
10. Yang C., Murray W.V., Wilson L.J. Tetrahedron Lett. 44:2003;1783-1786.
11. Ciganek E. Org. React. 51:1997;201-350.
12. Basavaiah D., Rao A.J., Satyanarayana T. Chem. Rev. 103:2003;811-892.
13. Baylis, A. B.; Hillman, M. E. D. Offenlegungsschrift 2155113, 1972; U.S. Patent 3,743669; Chem. Abstr. 1972, 77, 34174q.
14. This transformation was, however, originally reported by Morita and co-workers, see: Morita K., Suzuki Z., Hirose H. Bull. Chem. Soc. Jpn. 41:1968;2815-2816.
15. Perlmutter P., Teo C.C. Tetrahedron Lett. 25:1984;5951-5952.
16. Campi E.M., Holmes A., Perlmutter P., Teo C.C. Aust. J. Chem. 48:1995;1535-1540.
17. Balan D., Adolfsson H. J. Org. Chem. 66:2001;6498-6501.
18. Balan D., Adolfsson H. J. Org. Chem. 67:2002;2329-2334.
19. Balan D., Adolfsson H. Tetrahedron Lett. 44:2003;2521-2524.
20. The allylated aza-Baylis-Hillman adducts 4a-g were isolated in yields ranging from 95% to 99%.
21. For a general review on microwave assisted synthesis, see: Lidström P., Tierney J., Wathey B., Westman J. Tetrahedron. 57:2001;9225-9283.
22. Mayo K.G., Nearhoof E.H., Kiddle J.J. Org. Lett. 4:2002;1567-1570.
23. Garbacia S., Desai B., Lavastre O., Kappe C.O. J. Org. Chem. 68:2003;9136-9139.
24. For a recent discussion on the existence of nonthermal microwave effects, see: Kuhnert N. Angew. Chem., Int. Ed. 41:2002;1863-1866.
25. +).
26. For an alternative preparative route towards these heterocyclic compounds, see: Xu Z., Lu X. J. Org. Chem. 63:1998;5031-5041.
27. Fukuyama T., Jow C.-K., Cheung M. Tetrahedron Lett. 36:1995;6373-6374.