Synthesis of 2H-pyrroles via the 1,3-dipolar cycloaddition reaction of nitrile ylides with acrylamides

Tetrahedron Letters

Volumn 47, Issue 4, 2006, Pages 477-481

  Yoo, Choong Leol ^a   Olmstead, Marilyn M ^a   Tantillo, Dean J ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; BENZENE DERIVATIVE; CHLORIDE; NITRILE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CYCLOADDITION; METHODOLOGY; SYNTHESIS;

EID: 29144442039     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.066     Document Type: Article

References (33)

1. R. Huisgen, H. Stangl, H.J. Sturm, and H. Wagenhofer Angew. Chem. 74 1962 31
2. K. Bunge, R. Huisgen, R. Raab, and H. Stangl Chem. Ber. 105 1972 1279 1295
3. K. Bunge, R. Huisgen, R. Raab, and H.J. Sturm Chem. Ber. 105 1972 1307 1323
4. H.J. Hansen, and H. Heimgartner A. Padwa 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 Wiley New York 177 290
5. P.W. Groundwater, I. Garnett, A.J. Morton, T. Sharif, S.J. Coles, M.B. Hursthouse, M. Nyerges, R.J. Anderson, D. Bendell, A. McKillop, and W. Zhang J. Chem. Soc., Perkin Trans. 1 2001 2781 2787
6. A.F. Hegarty, S.J. Eustace, N.M. Tynan, N.-N. Pham-Tran, and M.T. Nguyen J. Chem. Soc., Perkin Trans. 2 2001 1239 1246
7. V. Nair, D. Sethumadhavan, S.M. Nair, S. Viji, and N.P. Rath Tetrahedron 58 2002 3003 3007
8. J.T. Sharp Chem. Heterocycl. Compounds 59 2002 473 537
9. S. Kanemasa Sci. Synth. 19 2004 67 78
10. N. Gakis, M. Maerky, H.J. Hansen, and H. Schmid Helv. Chim. Acta 55 1972 748 752
11. A. Padwa, S. Clough, M. Dharan, J. Smolanoff, and S.I. Wetmore Jr. J. Am. Chem. Soc. 94 1972 1395 1397
12. A. Padwa, M. Dharan, J. Smolanoff, and S.I. Wetmore Jr. J. Am. Chem. Soc. 95 1973 1945 1954
13. A. Inada, H. Heimgartner, and H. Schmid Tetrahedron Lett. 1979 2983 2986
14. W.-C. Cheng, Y. Liu, M. Wong, M.M. Olmstead, K.S. Lam, and M.J. Kurth J. Org. Chem. 67 2002 5673 5677
15. K.S.-L. Huang, E.H. Lee, M.M. Olmstead, and M.J. Kurth J. Org. Chem. 65 2000 499 503
16. S.H. Hwang, and M.J. Kurth J. Org. Chem. 67 2002 6564 6567
17. S.H. Hwang, M.M. Olmstead, and M.J. Kurth J. Comb. Chem. 6 2004 142 148
18. M.J. Kurth, L.A. Ahlberg Randall, and K. Takenouchi J. Org. Chem. 61 1996 8755 8761
19. K.-H. Park, M.M. Olmstead, and M.J. Kurth Synlett 2003 1267 1270
20. 3, 100 MHz) δ 172.3, 159.5, 150.6, 147.4, 140.5, 133.5, 133.0, 131.5, 130.6, 130.2, 129.0, 128.8, 128.1, 127.6, 123.0, 122.6, 114.1, 79.2, 55.5, 52.0, 51.2, 42.2.
21. R. Huisgen, H. Stangl, H.J. Sturm, R. Raab, and K. Bunge Chem. Ber. 105 1972 1258 1278
22. Calculations were performed with GAUSSIAN03 (M. J. Frisch, et al., Gaussian, Inc., Pittsburgh PA, 2003) using the B3LYP/6-311+G(d,p) method
23. (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652;
24. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377;
25. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789;
26. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627).
27. Related theoretical work by Gandolfi on diazoalkanes+olefins showed that non-planar dipolarophile geometries and methyl substitution decrease the reactivity of dipolarophiles: M. Burdisso, R. Gandolfi, S. Quartieri, and A. Rastelli Tetrahedron 43 1987 159 170
28. For conformational preferences of related molecules, see: Bastiansen, O.; Seip, H. M.; Boggs, J. E. In Dunitz, J. D., Ibers, J. A., Eds.; Perspectives in Structural Chemistry; Wiley: New York; 1971 Vol. 4, p 60.
29. K. Bunge, R. Huisgen, and R. Raab Chem. Ber. 105 1972 1296 1306
30. A.A. Ovcharenko, V.A. Chertkov, A.V. Karchava, and M.A. Yurovskaya Tetrahedron Lett. 38 1997 6933 6936
31. F.G. Bordwell, D. Algrim, and N.R. Vanier J. Org. Chem. 42 1977 1817 1819
32. 2-phenyl, and aza-allyl groups.
33. P. Zuman ARKIVOC 2002 85 140 and references cited therein