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Volumn 44, Issue 32, 2003, Pages 6073-6077

Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; THIOAMIDE; THIOUREA DERIVATIVE;

EID: 0038644140     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01469-2     Document Type: Article
Times cited : (197)

References (49)
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    • Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed. Springer-Verlag: New York
    • For reviews of palladium-catalyzed aminations, see: (a) Muci, A. R.; Buchwald, S. L. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219. Springer-Verlag: New York, 2002; pp. 131-209; (b) Hartwig, J. F. In Modern Amination Methods; Ricci, E., Ed.; Wiley-VCH, Weinheim, 2000; Chapter 7, pp. 195-262; (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (2002) Topics in Current Chemistry Ser. 219 , pp. 131-209
    • Muci, A.R.1    Buchwald, S.L.2
  • 2
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    • Ricci, E., Ed.; Wiley-VCH, Weinheim; Chapter 7
    • For reviews of palladium-catalyzed aminations, see: (a) Muci, A. R.; Buchwald, S. L. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219. Springer-Verlag: New York, 2002; pp. 131-209; (b) Hartwig, J. F. In Modern Amination Methods; Ricci, E., Ed.; Wiley-VCH, Weinheim, 2000; Chapter 7, pp. 195-262; (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (2000) Modern Amination Methods , pp. 195-262
    • Hartwig, J.F.1
  • 3
    • 0001038733 scopus 로고    scopus 로고
    • For reviews of palladium-catalyzed aminations, see: (a) Muci, A. R.; Buchwald, S. L. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219. Springer-Verlag: New York, 2002; pp. 131-209; (b) Hartwig, J. F. In Modern Amination Methods; Ricci, E., Ed.; Wiley-VCH, Weinheim, 2000; Chapter 7, pp. 195-262; (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 805-818
    • Wolfe, J.P.1    Wagaw, S.2    Marcoux, J.F.3    Buchwald, S.L.4
  • 4
    • 0032541260 scopus 로고    scopus 로고
    • For reviews of palladium-catalyzed aminations, see: (a) Muci, A. R.; Buchwald, S. L. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219. Springer-Verlag: New York, 2002; pp. 131-209; (b) Hartwig, J. F. In Modern Amination Methods; Ricci, E., Ed.; Wiley-VCH, Weinheim, 2000; Chapter 7, pp. 195-262; (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2046-2067
    • Hartwig, J.F.1
  • 27
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    • For recent reviews, see: (a) Kondo, T.; Mitsudo, T.-A. Chem. Rev. 2000, 100, 3205-3220; (b) Baranano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287-305.
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    • Kondo, T.1    Mitsudo, T.-A.2
  • 28
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    • For recent reviews, see: (a) Kondo, T.; Mitsudo, T.-A. Chem. Rev. 2000, 100, 3205-3220; (b) Baranano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287-305.
    • (1997) Curr. Org. Chem. , vol.1 , pp. 287-305
    • Baranano, D.1    Mann, G.2    Hartwig, J.F.3
  • 43
    • 0037507061 scopus 로고
    • A direct synthesis of benzothiazole from o-bromoaniline and thiourea using a niquel catalyst has been reported. See:
    • A direct synthesis of benzothiazole from o-bromoaniline and thiourea using a niquel catalyst has been reported. See: Takagi K. Chem. Lett. 1986;265-266.
    • (1986) Chem. Lett. , pp. 265-266
    • Takagi, K.1
  • 49
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    • 3 (1.5 mmol) were added. The resulting solution was heated to 80°C until the starting material had disappeared. The reaction mixture was then cooled, filtered over Celite, evaporated to dryness and purified by column chromatography
    • 3 (1.5 mmol) were added. The resulting solution was heated to 80°C until the starting material had disappeared. The reaction mixture was then cooled, filtered over Celite, evaporated to dryness and purified by column chromatography.


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