The application of vinylogous iminium salts and related synthons to the regiocontrolled preparation of 2,3- and 2,5-disubstituted pyrroles

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 6879-6892

  Gupton, John T ^a   Petrich, Scott A ^b   Smith, Lana L ^b   Bruce, Marc A ^b   Vu, Phong ^b   Du, Karen X ^b   Dueno, Eric E ^b   Jones, Claude R ^c   Sikorski, James A ^c  

^a UNIVERSITY OF NORTH CAROLINA AT ASHEVILLE   (United States)

^b UNIVERSITY OF CENTRAL FLORIDA   (United States)

^c MONSANTO COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029873091     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00338-9     Document Type: Article

References (9)

1. a. E. D. Edstrom and Y. Wei, J. Org. Chem., 1993, 58, 403;
2. b. T. Sakamoto, Y. Kondo, S. Sato and H. Yamanaka, Tetrahedron Lett., 1994, 35, 2919.
3. For some recent pyrrole syntheses see a; W. W. Wilkerson, W. Galbraith, K. Gans-Brangs, M. Grubb, W. E. Hewes, B. Jaffee, J. P. Kenney, J. Kerr and N. Wong, J. Med. Chem., 1994, 37, 988;
4. b; A. Padwa and Norman, B. H. Norman, J. Org. Chem., 1990, 55, 4801.
5. J. T. Gupton, D. A. Krolikowski, R. H. Yu, J. A. Sikorski and S. W. Riesinger, J. Org. Chem., 1990, 55, 4735.
6. J. T. Gupton, D. A. Krolikowski, R. H. Yu and P. Vu, J. A. Sikorski, M. L. Dahl and C. R. Jones, J. Org. Chem., 1992 , 57, 5480.
7. J. Liebscher and H. Hartman, Synthesis, 1979, 241.
8. E. Pretsch, T. Clerc, J. Seibl and W. Simon, Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, 1989, H265.
9. IR spectra were recorded on a Perkin-Elmer 1600 FTIR and NMR spectra were obtained with a Varian Gemini 200 spectrometer. All melting points and boiling points are uncorrected.