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Volumn 49, Issue 5, 2008, Pages 903-905

Synthesis of pyridazines functionalized with amino acid side chains

Author keywords

Inverse electron demand Diels Alder reaction; Pyridazine; Tebbe reagent; Tetrazine

Indexed keywords

AMINO ACID; ESTER DERIVATIVE; ETHER DERIVATIVE; PYRIDAZINE DERIVATIVE; TETRAZINE DERIVATIVE;

EID: 37749031444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.149     Document Type: Article
Times cited : (14)

References (27)
  • 14
    • 37749018557 scopus 로고    scopus 로고
    • Moisan, L.; Dale, T. J.; Gombosuren, N.; Biros, S. M.; Mann, E.; Hou, J. L.; Rebek J. Jr. Heterocycles 2007, available from: COM-07-S(U)45.
  • 18
    • 10844242809 scopus 로고    scopus 로고
    • Naud S. Synlett (2004) 2836-2837
    • (2004) Synlett , pp. 2836-2837
    • Naud, S.1
  • 22
    • 84985261706 scopus 로고
    • For previous use of cyclic or acyclic enol ethers as dienophiles for the IEDDAR with tetrazines see:
    • For previous use of cyclic or acyclic enol ethers as dienophiles for the IEDDAR with tetrazines see:. Gnichtel H., and Gumprecht C. Liebigs Ann. Chem. 3 (1985) 628-632
    • (1985) Liebigs Ann. Chem. , vol.3 , pp. 628-632
    • Gnichtel, H.1    Gumprecht, C.2
  • 27
    • 33947093052 scopus 로고
    • Tebbe reagent: μ-Chlorobis(cyclopentadienyl)-(dimethylaluminium)-μ-methylenetitan ium, Representative general procedure: To a solution of the corresponding ester (1.04 mmol) in THF (12 ml) cooled at -40 °C is added Tebbe reagent (2.7 ml, 1.3 equiv, 0.5 M in toluene). After 30 min the temperature is raised to ambient over a period of 2 h. The mixture is then cooled to -10 °C and the reaction is quenched by the dropwise addition of NaOH (700 μl, 2 M solution). Reaction mixture is then allowed to warm to room temperature. The solution is then diluted with excess of ether and filtered through a pad of Celite. Solvent is removed under reduced pressure and the crude residue is directly diluted in dioxane (10 ml) and added to a solution of tetrazine 1 (203 mg, 1.0 mmol) in dioxane (10 ml). After 18 h at room temperature, volatiles are removed and the crude residue is purified on silica gel (hexane/AcOEt mixtures) to afford the desired products
    • Tebbe reagent: μ-Chlorobis(cyclopentadienyl)-(dimethylaluminium)-μ-methylenetitan ium,. Tebbe F.N., Parshall G.W., and Reddy G.S. J. Am. Chem. Soc. 100 (1978) 3611-3613 Representative general procedure: To a solution of the corresponding ester (1.04 mmol) in THF (12 ml) cooled at -40 °C is added Tebbe reagent (2.7 ml, 1.3 equiv, 0.5 M in toluene). After 30 min the temperature is raised to ambient over a period of 2 h. The mixture is then cooled to -10 °C and the reaction is quenched by the dropwise addition of NaOH (700 μl, 2 M solution). Reaction mixture is then allowed to warm to room temperature. The solution is then diluted with excess of ether and filtered through a pad of Celite. Solvent is removed under reduced pressure and the crude residue is directly diluted in dioxane (10 ml) and added to a solution of tetrazine 1 (203 mg, 1.0 mmol) in dioxane (10 ml). After 18 h at room temperature, volatiles are removed and the crude residue is purified on silica gel (hexane/AcOEt mixtures) to afford the desired products
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3611-3613
    • Tebbe, F.N.1    Parshall, G.W.2    Reddy, G.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.