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Volumn 70, Issue 15, 2005, Pages 5938-5945

Palladium-catalyzed regioselective arylation of imidazo[1,2-b][1,2,4] triazine: Synthesis of an α2/3-selective GABA agonist

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CATALYSIS; CHROMATOGRAPHY; HALOGENATION; METHANE; PALLADIUM; SYNTHESIS (CHEMICAL);

EID: 22244485005     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0507035     Document Type: Article
Times cited : (72)

References (55)
  • 6
    • 32744454479 scopus 로고    scopus 로고
    • Preparation of 7-phenylimidazo[1,2-b][1,2,4]triazines as ligands for GABA receptors. PCT Int. Appl. 2003, 42 pp; WO 2003008418
    • Carling, W. R.; Hallett, D. J.; Russell, M. G. N.; Street, L. J. Preparation of 7-phenylimidazo[1,2-b][1,2,4]triazines as ligands for GABA receptors. PCT Int. Appl. 2003, 42 pp; WO 2003008418.
    • Carling, W.R.1    Hallett, D.J.2    Russell, M.G.N.3    Street, L.J.4
  • 21
    • 32744457604 scopus 로고    scopus 로고
    • note
    • 2 (75% yield).
  • 27
    • 32744472642 scopus 로고    scopus 로고
    • note
    • A sample of Grignard reagent 8a was quenched with water and a GC assay revealed 20:1 selectivity of 4-bromofluorobenzene versus 2-bromofluorobenzene.
  • 30
    • 32744477471 scopus 로고    scopus 로고
    • note
    • Only strong protic acids affected the desired bromination.
  • 31
    • 32744460891 scopus 로고    scopus 로고
    • note
    • 2O, whereas the succinamide generated by using NBS inhibited crystallization of the product.
  • 37
    • 32744467439 scopus 로고    scopus 로고
    • note
    • The regioselectivity was found to be highly pH dependent and gave optimal selectivity at pH 8-9.
  • 38
    • 32744470400 scopus 로고    scopus 로고
    • note
    • Cyclic byproduct 19a was found to be extremely stable to the hydrolysis conditions. Thus, once formed it does not convert back to keto aldehyde 17.
  • 42
    • 32744464723 scopus 로고    scopus 로고
    • Preparation of imidazotriazines as ligands for GABA receptors. PCT Int. Appl. 2003, 67 pp; WO 2003093272
    • Bettati, M.; Chambers, M. S.; Goodacre, S. C.; Hallett, D. J.; Russell, M. G. N.; Street, L. J. Preparation of imidazotriazines as ligands for GABA receptors. PCT Int. Appl. 2003, 67 pp; WO 2003093272.
    • Bettati, M.1    Chambers, M.S.2    Goodacre, S.C.3    Hallett, D.J.4    Russell, M.G.N.5    Street, L.J.6
  • 43
    • 32744454607 scopus 로고    scopus 로고
    • note
    • 2 in HOAc; see ref 5.
  • 49
    • 32744461574 scopus 로고    scopus 로고
    • note
    • Only a few parts per million of a heavy metal such as palladium can be tolerated in an API according to the guidelines of the International Conference on Harmonization (ICH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.