Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters

Tetrahedron Letters

Volumn 49, Issue 22, 2008, Pages 3691-3696

  Carafa, Marianna ^a   Distaso, Monica ^a   Mele, Valentina ^a   Trani, Francesca ^a   Quaranta, Eugenio ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Carbonylation; Catalysis; Organic carbonates; Phosgene substitution; Pyrrole

Indexed keywords

1 BENZYLOXYCARBONYLPYRROLE; 1 METHYLPYRROLE; 1 PHENOXYCARBONYLINDOLE; 1 TERT BUTYLOXYCARBONYLPYRROLE; 9 PHENOXYCARBONYLCARBAZOLE; BASE; CARBONIC ACID DERIVATIVE; DIMETHYLCARBONATE; DIPHENYLCARBONATE; METHYLPHENYLCARBONATE; PHOSGENE; PYRROLE; PYRROLE DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYST; SYNTHESIS;

EID: 43049150439     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.129     Document Type: Article

References (39)

1. Delledonne D., Rivetti F., and Romano U. Appl. Catal. A: Gen. 221 (2001) 241-251
2. Vauthey I., Valot F., Gozzi C., Fache F., and Lemaire M. Tetrahedron Lett. 41 (2000) 6347-6350
3. Distaso M., and Quaranta E. J. Catal. 228 (2004) 36-42
4. Distaso M., and Quaranta E. Appl. Catal. B: Environ. 66 (2006) 72-80
5. Distaso M., and Quaranta E. J. Catal. 253 (2008) 278-288
6. Most of studies have focused on the use of dialkyl carbonates as alkylating agents of indoles, benzimidazole and carbazole. See:. Shieh W.-C., Dell S., Bach A., Repic O., and Blacklock T. J. Org. Chem. 68 (2003) 1954-1957
7. Shieh W.-C., Lozanov M., Loo M., Repic O., and Blacklock T. Tetrahedron Lett. 44 (2003) 4563-4565
8. Shieh W.-C., Lozanov M., and Repic O. Tetrahedron Lett. 44 (2003) 6943-6945
9. Shieh W.-C., Dell S., and Repic O. Org. Lett. 3 (2001) 4279-4281
10. Jiang X., Tiwari A., Thompson M., Chen Z., Cleary T.P., and Lee T.B.K. Org. Process Res. Dev. 5 (2001) 604-608
11. Natsume M., and Muratake H. Tetrahedron Lett. 36 (1979) 3477-3480
12. Pandey G., Tiwari S.K., Singh R.S., and Mali R.S. Tetrahedron Lett. 42 (2001) 3947-3949
13. Paparin J.-L., Crévisy C., and Grée L. Eur. J. Org. Chem. (2000) 3909-3918
14. Scott M.S., Luckhurst C.A., and Dixon D.J. Org. Lett. 7 (2005) 5813-5816
15. Davies H.M.L., Saikali E., and Young W.B. J. Org. Chem. 56 (1991) 5696-5700
16. Von Becker H.G.O., and Richter H.J. J. Prakt. Chem. 316 (1974) 1013-1029
17. Matsunaga S., Kinoshita T., Okada S., Harada H., and Shibasaki M. J. Am. Chem. Soc. 126 (2004) 7559-7570
18. Evans D.A., Borg G., and Scheidt K.A. Angew. Chem., Int. Ed. 41 (2002) 3188-3191
19. Grehn L., and Ragnarsson U. Angew. Chem., Int. Ed. 23 (1984) 300-301
20. Carpino L.A., and Barr D.E. J. Org. Chem. 31 (1966) 764-767
21. Bergman J., Carlsson R., and Sjoberg B. J. Heterocycl. Chem. 14 (1977) 1123-1133
22. Gabel N. J. Org. Chem. 27 (1962) 301-303
23. Acheson R.M., and Vernon J.M. J. Chem. Soc., Chem. Commun. (1961) 457-459
24. Wang N.C., and Anderson H.J. Can J. Chem. 55 (1977) 4103-4111
25. Boger D.L., and Patel M. J. Org. Chem. 52 (1987) 2319-2323
26. Loader C.E., and Anderson H.J. Can J. Chem. 49 (1971) 45-48
27. Dhanak D., and Reese C.B. J. Chem. Soc., Perkin Trans. 1: Org. Bio-Org. Chem. (1972-1999) 12 (1986) 2181-2186
28. Ouk S., Thiébaud S., Borredon E., and Chabaud B. Synth. Commun. 35 (2005) 3021-3026
29. Itahara T. Heterocycles 24 (1986) 2557-2562
30. Boger D.L., and Patel M. J. Org. Chem. 52 (1987) 3934-3936
31. Macor J.E., Cuff A., and Cornelius L. Tetrahedron Lett. 40 (1999) 2733-2736
32. Jacquemard U., Benéteau V., Lefoix M., Routier S., Mérour J.-Y., and Coudert G. Tetrahedron Lett. 60 (2004) 10039-10047
33. Schwesinger R., Willaredt J., Schlemper H., Keller M., Schmitt D., and Fritz H.. Chem. Ber. 127 (1994) 2435-2454
34. Tundo P., and Selva M. Acc. Chem. Res. 35 (2002) 706-716
35. Barcelo G., Grenouillat J.-P., and Sennyey G. Tetrahedron 46 (1990) 1839-1848
36. Braunstein P., Lakkis M., and Matt D. J. Mol. Catal. 42 (1987) 353-355
37. -1): 1748vs (CO).
38. Stratton J., Gatlin B., and Venkatasubban K.S. J. Org. Chem. 57 (1992) 3237-3240
39. See also. Carpino L.A., Carpino B.A., Giza C.A., Murray R.W., Santilli A.A., and Terry P.A. Org. Synth. 44 (1964) 22-25