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Volumn 5, Issue 3, 2003, Pages 205-207

Attachment of unreactive amines to the solid support: Synthesis of phenyl-substituted anilines, 2-aminopyridines, and 2-aminopyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID DERIVATIVE; AMINOPYRIDINE DERIVATIVE; ANILINE; ANILINE DERIVATIVE; CARBAMIC ACID; DIPEPTIDE; POLYSTYRENE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

EID: 0141563670     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0201039     Document Type: Article
Times cited : (18)

References (23)
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    • For other representative examples, see (a) Li, W.-R.; Lin, Y.-S.; Yo, Y.-C. Tetrahedron Lett. 2000, 41, 6619-6622. (b) Morton, G. C.; Salvino, J. M.; Labaudinière, R. F.; Herpin, T. F. Tetrahedron Lett. 2000, 41, 3029-3033. (c) Rossė, G.; Ouertani, F.; Schröder, H. J. Comb. Chem. 1999, 1, 397-401. (d) Veerman, J. J. N.; Rutjes, F. P. J. T.; van Maarseveen, J. H.; Hiemstra, H. Tetrahedron Lett. 1999, 40, 6079-6082. (e) Dressman, B. A.; Singh, U.; Kaldor, S. W. Tetrahedron Lett. 1998, 39, 3631-3634. (f) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031-3034.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3029-3033
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    • 0000629489 scopus 로고    scopus 로고
    • For other representative examples, see (a) Li, W.-R.; Lin, Y.-S.; Yo, Y.-C. Tetrahedron Lett. 2000, 41, 6619-6622. (b) Morton, G. C.; Salvino, J. M.; Labaudinière, R. F.; Herpin, T. F. Tetrahedron Lett. 2000, 41, 3029-3033. (c) Rossė, G.; Ouertani, F.; Schröder, H. J. Comb. Chem. 1999, 1, 397-401. (d) Veerman, J. J. N.; Rutjes, F. P. J. T.; van Maarseveen, J. H.; Hiemstra, H. Tetrahedron Lett. 1999, 40, 6079-6082. (e) Dressman, B. A.; Singh, U.; Kaldor, S. W. Tetrahedron Lett. 1998, 39, 3631-3634. (f) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031-3034.
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    • Rosse, G.1    Ouertani, F.2    Schröder, H.3
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    • 0033551728 scopus 로고    scopus 로고
    • For other representative examples, see (a) Li, W.-R.; Lin, Y.-S.; Yo, Y.-C. Tetrahedron Lett. 2000, 41, 6619-6622. (b) Morton, G. C.; Salvino, J. M.; Labaudinière, R. F.; Herpin, T. F. Tetrahedron Lett. 2000, 41, 3029-3033. (c) Rossė, G.; Ouertani, F.; Schröder, H. J. Comb. Chem. 1999, 1, 397-401. (d) Veerman, J. J. N.; Rutjes, F. P. J. T.; van Maarseveen, J. H.; Hiemstra, H. Tetrahedron Lett. 1999, 40, 6079-6082. (e) Dressman, B. A.; Singh, U.; Kaldor, S. W. Tetrahedron Lett. 1998, 39, 3631-3634. (f) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031-3034.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6079-6082
    • Veerman, J.J.N.1    Rutjes, F.P.J.T.2    Van Maarseveen, J.H.3    Hiemstra, H.4
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    • 0032575179 scopus 로고    scopus 로고
    • For other representative examples, see (a) Li, W.-R.; Lin, Y.-S.; Yo, Y.-C. Tetrahedron Lett. 2000, 41, 6619-6622. (b) Morton, G. C.; Salvino, J. M.; Labaudinière, R. F.; Herpin, T. F. Tetrahedron Lett. 2000, 41, 3029-3033. (c) Rossė, G.; Ouertani, F.; Schröder, H. J. Comb. Chem. 1999, 1, 397-401. (d) Veerman, J. J. N.; Rutjes, F. P. J. T.; van Maarseveen, J. H.; Hiemstra, H. Tetrahedron Lett. 1999, 40, 6079-6082. (e) Dressman, B. A.; Singh, U.; Kaldor, S. W. Tetrahedron Lett. 1998, 39, 3631-3634. (f) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031-3034.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3631-3634
    • Dressman, B.A.1    Singh, U.2    Kaldor, S.W.3
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    • For other representative examples, see (a) Li, W.-R.; Lin, Y.-S.; Yo, Y.-C. Tetrahedron Lett. 2000, 41, 6619-6622. (b) Morton, G. C.; Salvino, J. M.; Labaudinière, R. F.; Herpin, T. F. Tetrahedron Lett. 2000, 41, 3029-3033. (c) Rossė, G.; Ouertani, F.; Schröder, H. J. Comb. Chem. 1999, 1, 397-401. (d) Veerman, J. J. N.; Rutjes, F. P. J. T.; van Maarseveen, J. H.; Hiemstra, H. Tetrahedron Lett. 1999, 40, 6079-6082. (e) Dressman, B. A.; Singh, U.; Kaldor, S. W. Tetrahedron Lett. 1998, 39, 3631-3634. (f) Kaljuste, K.; Undén, A. Tetrahedron Lett. 1996, 37, 3031-3034.
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    • 0032514431 scopus 로고    scopus 로고
    • The same concept has been used to displace imidazole from the carbonylimidazole resin. See: Josey, J. A.; Tarlton, C. A.; Payne, C. E. Tetrahedron Lett. 1998, 39, 5899-5902.
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    • note
    • The general procedure for the carbamate formation can be found in the Supporting Information of this Report.
  • 19
    • 0002780599 scopus 로고    scopus 로고
    • The yield was determined by NMR with 2,5-dimethylfuran (DMFu) as internal standard. Gerritz, S. W.; Sefler, A. M. J. Comb. Chem. 2000, 2, 39-41.
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    • Gerritz, S.W.1    Sefler, A.M.2
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    • 0141582198 scopus 로고    scopus 로고
    • note
    • The modified procedure can be found in the Supporting Information of this Report.
  • 21
    • 0141693832 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum with a known sample of 4-bromoaniline, this compound was >95% pure.
  • 23
    • 0141693831 scopus 로고    scopus 로고
    • note
    • The conditions for the Suzuki coupling described in the Supporting Information gave the products with the highest yield and purity among the variations we attempted.


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