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Volumn , Issue 19, 2007, Pages 3016-3018

Polysubstituted thiazole derivatives via the halogen-dance reaction

Author keywords

Halogen dance; Lithiation; Metalation; Thiazole

Indexed keywords

4 BROMO 2 CHLOROTHIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 37248998790     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992354     Document Type: Article
Times cited : (11)

References (35)
  • 10
    • 37249004482 scopus 로고    scopus 로고
    • Murakami, H.; Takii, S.; Mizuno, M. JP 200466855, 2005; Chem. Abstr. 2005, 143, 306303.
    • (b) Murakami, H.; Takii, S.; Mizuno, M. JP 200466855, 2005; Chem. Abstr. 2005, 143, 306303.
  • 12
    • 37249044925 scopus 로고    scopus 로고
    • DE 10134478, 137301
    • (d) Doemling, A.; Kolb, J. DE 10134478, 2003; Chem. Abstr. 2003, 138, 137301.
    • (2003) Chem. Abstr , vol.138
    • Doemling, A.1    Kolb, J.2
  • 13
    • 0009860323 scopus 로고    scopus 로고
    • Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom
    • Schaumann, E, Ed, Georg Thieme Verlag: Stuttgart
    • Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom, In Science of Synthesis, Vol. 11; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 2002, 627.
    • (2002) Science of Synthesis , vol.11 , pp. 627
  • 18
    • 13644268558 scopus 로고    scopus 로고
    • and references cited therein
    • (a) Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245; and references cited therein.
    • (2005) Tetrahedron , vol.61 , pp. 2245
    • Schröter, S.1    Stock, C.2    Bach, T.3
  • 33
    • 37249036201 scopus 로고    scopus 로고
    • General Procedure for the HD Reaction and Quenching with Electrophiles to Compounds 2a-h: To a solution of 5-bromo-2-chlorothiazole (1, 199 mg, 1 mmol, 1 equiv) in anhydrous THF under argon atmosphere a freshly prepared solution of LDA (1.2 equiv) in anhydrous THF was added at -80°C and the mixture stirred at that temperature until TLC analysis showed complete HD reaction (15-20 min, Then the corresponding electrophile (1.5 equiv) was added at -80°C and the reaction was allowed to warm to r.t. The reaction mixture was poured into 2 N HCl and the aqueous phase was extracted with Et 2O. The organic layer was washed with 2 N HCl (2x, H2O (2x) and brine 2x, dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified either by column chromatography or by Kugelrohr distillation
    • 4, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified either by column chromatography or by Kugelrohr distillation.
  • 34
    • 37249091387 scopus 로고    scopus 로고
    • 3): δ = 72.9 (s, C5), 132.6 (s, C4), 156.3 (s, C2).
    • 3): δ = 72.9 (s, C5), 132.6 (s, C4), 156.3 (s, C2).
  • 35
    • 37249008367 scopus 로고    scopus 로고
    • 3): δ = 132.1 (s), 134.9 (s), 160.1 (s, C2), 181.9 (d, CHO).
    • 3): δ = 132.1 (s), 134.9 (s), 160.1 (s, C2), 181.9 (d, CHO).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.