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Volumn 51, Issue 32, 2010, Pages 4229-4232

Acyl pyruvates as synthons in the Biginelli reaction

Author keywords

Acyl pyruvates; Biginelli reaction; Dihydropyrimidines; Heterocycles; Multicomponent reactions

Indexed keywords

BUTYRIC ACID DERIVATIVE; CHLOROTRIMETHYLSILANE; PYRUVIC ACID DERIVATIVE; THIOUREA DERIVATIVE;

EID: 77955308933     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.032     Document Type: Article
Times cited : (36)

References (60)
  • 49
    • 27744533753 scopus 로고    scopus 로고
    • Several examples of solid-phase synthesis of 3,4-dihydropyrimidine-2-ones employing phenylpyruvic and 2-oxobutyric acids as the methylene component have been reported recently, see: W. Li, and Y. Lam J. Comb. Chem. 7 2005 721 725
    • (2005) J. Comb. Chem. , vol.7 , pp. 721-725
    • Li, W.1    Lam, Y.2
  • 50
    • 77955307583 scopus 로고    scopus 로고
    • note
    • General procedure for the Biginelli reactions. A mixture of ester 5 (4 mmol), benzaldehyde (4 mmol), thiourea 6 (6 mmol), and dry DMF (10 mL) was sonicated for 1 h at rt to dissolve the starting materials, and then chlorotrimethylsilane (16 mmol) was added dropwise. The resulting mixture was allowed to stand for 3-4 d and then poured into water (20-30 mL). The suspension was sonicated for 1 h and the precipitate was filtered and washed with a small amount of iPrOH. The filtrate was evaporated under reduced pressure, and the residue was triturated with a small amount of iPrOH and filtered again. The combined solids were recrystallized to yield the products 7-9 (see Schemes 2-4 ).
  • 51
    • 77955307859 scopus 로고    scopus 로고
    • note
    • 4: C, 68.56; H, 5.18; N, 8.00. Found: C, 68.42; H, 5.30; N, 8.08.
  • 52
    • 77955309125 scopus 로고    scopus 로고
    • note
    • 4: C, 72.35; H, 4.55; N, 7.03. Found: C, 72.62; H, 4.28; N, 6.97.
  • 55
    • 77955309334 scopus 로고    scopus 로고
    • See Ref. 9d and citations therein
    • See Ref. 9d and citations therein.
  • 58
    • 77955303602 scopus 로고    scopus 로고
    • note
    • ++1 = 399.
  • 59
    • 77955309404 scopus 로고    scopus 로고
    • Final atomic coordinates, geometrical parameters, and crystallographic data have been deposited with the Cambridge Crystallographic Data Centre, 11 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 336033
    • Final atomic coordinates, geometrical parameters, and crystallographic data have been deposited with the Cambridge Crystallographic Data Centre, 11 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk ) and are available on request quoting the deposition number CCDC 759878 (10a) and CCDC 759879 (10b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.