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Volumn 52, Issue 20, 2011, Pages 2536-2539

One pot spiropyrazoline synthesis via intramolecular cyclization/ methylation

Author keywords

Cycloaddition; Heterocycles; Intramolecular cyclization; Regioselectivity; Spirocycles; Spiropyrazolines

Indexed keywords

5,5 PYRAZOLINE DERIVATIVE; ALKENE; AROMATIC COMPOUND; ELECTROPHILE; ESTER DERIVATIVE; FUNCTIONAL GROUP; IMINE; NUCLEOPHILE; PYRAZOLINE DERIVATIVE; SPIROPYRAZOLINE; UNCLASSIFIED DRUG;

EID: 79954594409     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.004     Document Type: Article
Times cited : (22)

References (97)
  • 15
    • 0347573618 scopus 로고    scopus 로고
    • U.S. Patent 5,859,257, 1999
    • Talley, J. J. U.S. Patent 5,859,257, 1999; Chem. Abstr. 1999, 130, 110269.
    • (1999) Chem. Abstr. , vol.130 , pp. 110269
    • Talley, J.J.1
  • 17
    • 0033288941 scopus 로고    scopus 로고
    • Selective Inhibitors of COX-2
    • J.J. Talley Selective Inhibitors of COX-2 F.D. King, A. Oxford, Progress in Medicinal Chemistry Vol. 36 1999 Elsevier Amsterdam 201 234
    • (1999) Progress in Medicinal Chemistry , vol.36 , pp. 201-234
    • Talley, J.J.1
  • 21
  • 94
    • 79954606543 scopus 로고    scopus 로고
    • note
    • General procedure for the synthesis of [2+3]-cycloaddition products: A solution of the functionalized alkene (3.0 mmol) and the hydrazonyl chloride (3.0 mmol) in 10 mL of either dry chloroform or dichloromethane was treated with triethylamine (0.463 mL, 3.3 mmol). The reaction mixture was stirred at rt until the disappearance of the starting materials, as evidenced by TLC. After the reaction was complete, the crude reaction mixture was concentrated, and the solvent was evaporated under reduced pressure. The crude products were purified by flash column chromatography over silica gel by using the appropriate hexanes-ethyl acetate ratio as an eluant system.
  • 95
    • 79954604807 scopus 로고    scopus 로고
    • note
    • General procedure for the intramolecular cyclization/alkylation: To a solution of the cycloaddition product (1.0 mmol) in 15 mL of anhydrous toluene was added potassium tert-butoxide (6-8 mmol). The reaction mixture was then allowed to stir under anhydrous conditions until the disappearance of the starting materials, as evidenced by TLC. To this mixture was added 2 equiv of dimethyl sulfate (2 mmol, 0.186 mL), and the reaction mixture was heated to reflux temperature for 8 h under anhydrous conditions. The reaction mixture was later quenched with saturated ammonium chloride and extracted with EtOAc. The crude reaction mixture was concentrated, and the solvent was evaporated under reduced pressure. The crude products were purified by flash column chromatography over silica gel by using the appropriate hexanes-ethyl acetate ratio as an eluant system.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.