메뉴 건너뛰기




Volumn 48, Issue 8, 2007, Pages 1349-1352

A highly regio- and chemoselective addition of carbon nucleophiles to pyrimidinones. A new route to C4 elaborated Biginelli compounds

Author keywords

Biginelli compounds; Carbon nucleophiles; Lithiation; Regioselective addition

Indexed keywords

CARBON; CARBOXYLIC ACID DERIVATIVE; PYRIMIDINONE DERIVATIVE;

EID: 33846339316     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.111     Document Type: Article
Times cited : (32)

References (20)
  • 14
    • 0141939774 scopus 로고
    • Contrary to our findings, C4 unsubstituted dihydropyrimidinones lacking a C5 ester substituent have shown variation in reactivity depending upon the reagent used. Whereas only MeLi could be added at C-4, RMgX invariably reacted at C-6, see:
    • Contrary to our findings, C4 unsubstituted dihydropyrimidinones lacking a C5 ester substituent have shown variation in reactivity depending upon the reagent used. Whereas only MeLi could be added at C-4, RMgX invariably reacted at C-6, see:. Kashima C., Katoh A., Yokota Y., and Omote Y. J. Chem. Soc., Perkin Trans. 1 (1981) 489-492
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 489-492
    • Kashima, C.1    Katoh, A.2    Yokota, Y.3    Omote, Y.4
  • 16
    • 33846390109 scopus 로고    scopus 로고
    • note
    • To a solution of diisopropylamine (0.58 mL, 0.42 g, 4.42 mmol) in THF (2 mL), n-BuLi (1.85 mL, 2.2 M) was added dropwise at -78 °C, under a nitrogen atmosphere. The solution was allowed to warm to 0 °C and stirred for an additional 10 min. The solution was cooled to -78 °C and pre-cooled THF (25 mL at -78 °C) was added with stirring. The appropriate carbon acid, for example, acetone, acetonitrile, acetophenone (4.42 mmol), was then introduced via a glass syringe. The solution was stirred for an additional 10 min at the same temperature before use.
  • 17
    • 33846358584 scopus 로고    scopus 로고
    • note
    • Generated using n-BuLi (-78 °C).
  • 20
    • 33846336874 scopus 로고    scopus 로고
    • note
    • 4: C, 56.68; H, 7.13; N, 11.02; found: C, 56.40; H, 6.96; N, 10.86; MS: 277 (M+23).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.