Hantzsch pyrrole synthesis on solid support

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 17, 1998, Pages 2381-2384

  Trautwein, Axel W ^a   Süßmuth, Roderich D ^a   Jung, Günther ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; KETONE; PYRROLE DERIVATIVE;

ACETYLATION; ALKYLATION; AMINATION; ARTICLE; ENZYME IMMUNOASSAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; ORGANIC CHEMISTRY; SYNTHESIS;

ACETOACETATES; CHEMISTRY, ORGANIC; DRUG DESIGN; FLUORENES; INDICATORS AND REAGENTS; PHENETHYLAMINES; POLYSTYRENES; PYRROLES; RESINS, SYNTHETIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032497350     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00430-2     Document Type: Article

References (18)

1. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
2. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
3. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
4. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
5. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
6. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
7. 1. Reviews: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17. Combinatorial Peptide and Nonpeptide Libraries, Jung, G., Ed., VCH: Weinheim, 1996. Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411. Brown, R. Contemp. Org. Syn. 1997, 216.
8. 2. Review: Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
9. 3. Hantzsch, A. Chem. Ber. 1890, 23, 1474. Roomi, M. W.; MacDonald S. F. Can. J. Chem. 1970, 48, 1689.
10. 3. Hantzsch, A. Chem. Ber. 1890, 23, 1474. Roomi, M. W.; MacDonald S. F. Can. J. Chem. 1970, 48, 1689.
11. 4. The solid-phase synthesis of pyrroles using a four component condensation has recently been described, see: Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943.
12. 5. The solid-phase synthesis of 1,4-dihydropyridines using a Hantzsch condensation has recently been described, see: Gordeev, M. F.; Patel, D.V.; Wu, J.; Gordon, E. M. Tetrahedron Lett. 1996, 37, 4643.
13. 6. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
14. 7. Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431.
15. 8. Wilson, S. R.; Price, M. F. J. J. Org. Chem. 1984, 49, 722 and ref 14 cited therein.
16. 9. Kanner, B. Heterocycles 1982, 18, 411.
17. 2O. Cleavage is performed with 20% TFA in DCM for 30 min. The solution is concentrated to dryness to provide the crude pyrrole which is then lyophilized from tert-butyl alcohol/water (4/1).
18. 6) δ 10.9, 31.3, 51.5, 63.7, 111.4, 116.4, 124.1, 128.9, 130.1, 136.7, 138.7, 146.0, 166.2.