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Volumn 74, Issue 21, 2009, Pages 8460-8463

Synthesis of densely substituted pyrimidine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACID DERIVATIVE; AZA-HETEROCYCLES; CHEMICAL EQUATIONS; DERIVATIZATIONS; HETEROATOMS; PYRIMIDINE DERIVATIVES;

EID: 70350733535     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9017149     Document Type: Article
Times cited : (77)

References (54)
  • 1
    • 84944052334 scopus 로고    scopus 로고
    • For reviews, see: (a) Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, UK
    • For reviews, see: (a) Undheim, K.; Benneche, T. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, UK, 1996; Vol.6, p 93.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.6 , pp. 93
    • Undheim, K.1    Benneche, T.2
  • 4
    • 0004061168 scopus 로고    scopus 로고
    • 4th ed.; Blackwell Science Ltd.: Cambridge, MA
    • (d) Joule, J. A.; Mills, K. In Heterocyclic Chemistry, 4th ed.; Blackwell Science Ltd.: Cambridge, MA, 2000; p 194.
    • (2000) Heterocyclic Chemistry , pp. 194
    • Joule, J.A.1    Mills, K.2
  • 6
    • 85082699476 scopus 로고
    • For representative reports, see: (a)
    • For representative reports, see: (a) Madroñero, R.; Vega, S. Synthesis 1987, 628.
    • (1987) Synthesis , pp. 628
    • Madroñero, R.1    Vega, S.2
  • 29
  • 34
    • 64549146699 scopus 로고    scopus 로고
    • For a discussion on the nature of the activated amide as a function of amide structure, please see
    • For a discussion on the nature of the activated amide as a function of amide structure, please see: Medley, J. W.; Movassaghi, M. J. Org. Chem. 2009, 74, 1341.
    • (2009) J. Org. Chem. , vol.74 , pp. 1341
    • Medley, J.W.1    Movassaghi, M.2
  • 35
    • 70350744643 scopus 로고    scopus 로고
    • note
    • Treatment of amide 1b with thiocyanatobenzene provided the corresponding quinazoline in <15% yield under various reaction conditions.
  • 37
    • 70350730522 scopus 로고    scopus 로고
    • note
    • Treatment of amide 1a with cyanic bromide did give the corresponding 4-bromopyrimidine albeit in low yields (37-56%).
  • 38
    • 70350721307 scopus 로고    scopus 로고
    • note
    • We have considered mechanisms other than direct nucleophilic addition of 2e to an electrophilic intermediate; however, in the absence of any contrary data, a plausible mechanism based on our prior studies is used here.
  • 41
    • 70350731004 scopus 로고    scopus 로고
    • note
    • The use of trimethylsilyl cyanide led to decomposition of the activated amide.
  • 43
    • 70350730706 scopus 로고    scopus 로고
    • note
    • Cyanamide, bis(trimethylsilyl)carbodiimide, and potassium cyanate do not serve as competent nucleophiles under our condensative pyrimidine synthesis reaction conditions; for example, amide 1c and cyanamide did not afford 6u.
  • 54
    • 70350744813 scopus 로고    scopus 로고
    • note
    • A variety of 2-thiopyrimidine derivatives were synthesized in low yield (<20%) primarily due to the incomplete activation of the carbamothioates.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.