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Volumn 70, Issue 5, 2005, Pages 1957-1960

Efficient conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-one to pyrimidines via PyBroP-mediated coupling

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROGENATION; ORGANIC COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 14544306016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040281j     Document Type: Article
Times cited : (86)

References (41)
  • 24
    • 0042093870 scopus 로고    scopus 로고
    • Merck & Co., Inc.: Whitehouse Station
    • For representative drugs and biologicals containing pyrimidines (over 80 examples), such as amprolium, bispyribac, cetotiamine, diaveridine, ethirimol, fenarimol, glymidine, ipsapirone, lesopitron, mepanipyrin, nimustine, oxythiamine, peplomycin, quinapyramine, rimsulfuron, sulfabromomethazine,and tandospirone, see: The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals, 13th ed.; Merck & Co., Inc.: Whitehouse Station, 2001.
    • (2001) The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals, 13th Ed.
  • 30
    • 17444421249 scopus 로고    scopus 로고
    • Abstracts of Papers, Philadelphia, PA.; American Chemical Society: Washington, DC, ORGN 702
    • For a preliminary communication of this study, see: Kang, F.-A.; Murray, W. V. Abstracts of Papers, 228th National Meeting of the American Chemical Society, Philadelphia, PA.; American Chemical Society: Washington, DC, 2004; ORGN 702.
    • (2004) 228th National Meeting of the American Chemical Society
    • Kang, F.-A.1    Murray, W.V.2
  • 32
    • 14544275992 scopus 로고    scopus 로고
    • note
    • 6, see the Supporting Information.
  • 35
    • 0033051128 scopus 로고    scopus 로고
    • (c) The coupling reactions by directly using commercial PyBOP or PyBroP usually produce about 5% of the pyrolidine-containing side-product 3c (Table 2), which is attributed to the presence of a small amount of pyrrolidine as a contaminant to the commercial phosphonium salts. This side reaction does not occur when the reagents are recrystallized before their use in the coupling reaction. For recrystallization of PyBOP and PyBroP, and a similar observation of pyrolidine-containing side-product formation, see: Alsina, J.; Barany, G.; Albericio, F.; Kates, S. A. Lett. Peptide Sci. 1999, 6, 243.
    • (1999) Lett. Peptide Sci. , vol.6 , pp. 243
    • Alsina, J.1    Barany, G.2    Albericio, F.3    Kates, S.A.4
  • 36
    • 14544279855 scopus 로고    scopus 로고
    • note
    • PyBOP is slightly less efficient than PyBroP since it forms two transition intermediates with 2, the more reactive 4 (Table 2) and the less reactive 2-O-(benzotriazol-1-yl)-pyrimidine which can be isolated from the incomplete coupling reaction.
  • 37
    • 14544308422 scopus 로고    scopus 로고
    • note
    • It is interesting to note that the less effective solvents, e.g. MeCN, DCM and DMF led to homogeneous reactions, while the more effective solvents, e.g. dioxane, THF and DME, resulted in heterogeneous reactions. Dioxane seems to cause a slightly less heterogeneous, faster and cleaner reaction than THF and DME.
  • 38
    • 0033166435 scopus 로고    scopus 로고
    • It is not surprising that DMF was the least effective solvent for the targeted coupling reaction, since it is known that DMF can form formamidines with amines in the presence of PyBroP; see: Delarue, S.; Sergheraert, C. Tetrahedron Lett. 1999, 40, 5487.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5487
    • Delarue, S.1    Sergheraert, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.