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Volumn , Issue 34, 2007, Pages 5712-5716

New pyrimidylboronic acids and functionalized heteroarylpyrimidines by Suzuki cross-coupling reactions

Author keywords

Boronic acid; Cross coupling; Lithiation; Pyrimidine

Indexed keywords


EID: 36849035781     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700654     Document Type: Article
Times cited : (24)

References (64)
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    • Reviews of cross-coupling methodology: a) B. U. W. Maes, Top. Heterocycl. Chem. 2006, 1, 155-211;
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    • For a review of heterocyclic boronic acids
    • For a review of heterocyclic boronic acids: E. Tyrrell, P. Brookes, Synthesis 2003, 469-483.
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    • Eds, F. Diederich, A. de Meijere, Wiley-VCH, Weinheim, ch. 2;
    • c) N. Miyaura in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, A. de Meijere), Wiley-VCH, Weinheim, 2004, ch. 2;
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
    • Miyaura, N.1
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    • Reviews of lithiation of azines: a
    • Reviews of lithiation of azines: a) F. Mongin, G. Quéguiner, Tetrahedron 2001, 57, 4059-4090;
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    • Functionalized pyrimidines: a) V. Bonnet, F. Mongin, F. Trecourt, G. Queguiner, P. Knochel, Tetrahedron 2002, 58, 4429-4438;
  • 50
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    • For biologically significant azabiaryls: a
    • For biologically significant azabiaryls: a) T. T. Denton, X. Zhang, J. R. Cashman, J. Med. Chem. 2005, 48, 224-239;
    • (2005) J. Med. Chem , vol.48 , pp. 224-239
    • Denton, T.T.1    Zhang, X.2    Cashman, J.R.3
  • 53
    • 36849079683 scopus 로고    scopus 로고
    • Analogous lithiation/borylation procedures on 2-amino-5-bromopyridine and 1-amino-4-bromobenzene gave complex product mixtures; the corresponding boronic acid/ester derivatives could not be isolated
    • Analogous lithiation/borylation procedures on 2-amino-5-bromopyridine and 1-amino-4-bromobenzene gave complex product mixtures; the corresponding boronic acid/ester derivatives could not be isolated.
  • 54
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    • The isolated yields of cross-coupled products from in situ trapping of ester 9 were lower (based on 7) than from reactions via the purified acid 8.
    • The isolated yields of cross-coupled products from in situ trapping of ester 9 were lower (based on 7) than from reactions via the purified acid 8.
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    • For example, o-cyanopyridylboronic esters are more suitable than the corresponding boronic acids: T. Cailly, F. Fabis, A. Bouillon, S. Lemaître, J. Sopkova, O. de Santos, S. Rault, Synlett 2006, 53-56.
    • For example, o-cyanopyridylboronic esters are more suitable than the corresponding boronic acids: T. Cailly, F. Fabis, A. Bouillon, S. Lemaître, J. Sopkova, O. de Santos, S. Rault, Synlett 2006, 53-56.
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    • For examples of 2-arylbenzothiazoles for biomedical applications see: V. J. Majo, J. Prabhakaran, J. J. Mann, J. S. D. Kumar, Tetrahedron Lett. 2003, 44, 8535-8537
    • For examples of 2-arylbenzothiazoles for biomedical applications see: V. J. Majo, J. Prabhakaran, J. J. Mann, J. S. D. Kumar, Tetrahedron Lett. 2003, 44, 8535-8537.
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    • For other successful Suzuki reactions with halogenated substrates containing a primary amino group see: a) ref, 10j] b F. Bracher, J. Daab, Chem. 2002, 2288-2291
    • [10j] b) F. Bracher, J. Daab, Eur. J. Org. Chem. 2002, 2288-2291.
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    • For a related cyclization see
    • For a related cyclization see: E. F. DiMauro, J. R. Vitullo, J. Org. Chem. 2006, 71, 3959-3962.
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    • DiMauro, E.F.1    Vitullo, J.R.2
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    • As noted by a referee, the degassing procedure does not ensure that the solvent is free of peroxide
    • As noted by a referee, the degassing procedure does not ensure that the solvent is free of peroxide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.