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Volumn 5, Issue 6, 2001, Pages 581-586

Large-scale synthesis of a pyrrolo[2,3-d]pyrimidine via Dakin-West reaction and Dimroth rearrangement

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EID: 0035562117     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op010041v     Document Type: Article
Times cited : (40)

References (44)
  • 4
    • 0030992914 scopus 로고    scopus 로고
    • and references therein
    • (d) Traxler, P. Expert Opin. Ther. Pat. 1997, 7(6), 571 and references therein.
    • (1997) Expert Opin. Ther. Pat. , vol.7 , Issue.6 , pp. 571
    • Traxler, P.1
  • 14
    • 0002147039 scopus 로고
    • For a review on the Dakin-West reaction, see: Buchanan, G. L. Chem. Soc. Rev. 1988, 17, 91.
    • (1988) Chem. Soc. Rev. , vol.17 , pp. 91
    • Buchanan, G.L.1
  • 22
    • 84943926541 scopus 로고
    • (f) Knorr, R. Chem. Ber. 1971, 104, 3633.
    • (1971) Chem. Ber. , vol.104 , pp. 3633
    • Knorr, R.1
  • 24
    • 0040878545 scopus 로고    scopus 로고
    • note
    • This mechanism was originally proposed by Cleland and Niemann (see ref 9a); it only applies to the Dakin-West reaction of primary amino acids.
  • 25
    • 0040284216 scopus 로고    scopus 로고
    • note
    • For a typical lab-scale experiment in milligram or low-gram range, the amount of carbon dioxide evolved is certainly too small to be of any concern. Hence, there is no need for an alternative procedure to the Dakin-West reaction on lab scale.
  • 27
    • 0040284217 scopus 로고    scopus 로고
    • note
    • Safety remark: malonodinitrile decomposes autocatalytically at elevated temperatures with an adiabatic temperature rise in excess of 1000 °C! The initiation phase of the decomposition is shortened by bases. For these reasons, when performing this type of pyrrole condensation reactions on large scale, malonodinitrile should be the component being added to the sodium hydroxide solution rather than the opposite way to avoid a possible run-away reaction.
  • 28
    • 0040878543 scopus 로고    scopus 로고
    • note
    • Bulk substance was stored in barrels which were flushed with nitrogen to avoid pyrrole oxidation.
  • 35
    • 0039692513 scopus 로고    scopus 로고
    • U.S. Patent 2,684,976, 1954
    • Glickman, A. S. U.S. Patent 2,684,976, 1954.
    • Glickman, A.S.1
  • 36
    • 0039100269 scopus 로고    scopus 로고
    • note
    • This interpretation was later confirmed by applying the final, optimized procedure to different anilines: only those which gave pyrrolopyrimidines poorly soluble in ethanol and which were therefore precipitating from the reaction mixture could be prepared by this procedure.
  • 37
    • 0040878540 scopus 로고    scopus 로고
    • note
    • NMR investigations on the synthesis of iminoester 4b had shown earlier, that at lower temperature, amidine 4c was the predominant product in the mixture, and only by heating above 120 °C and with excess orthoformate, could iminoester 4b be obtained.
  • 38
    • 84995196749 scopus 로고
    • For a review on Dimroth rearrangements, see for example: Wahren, M. Z. Chem. 1969, 9(7), 241.
    • (1969) Z. Chem. , vol.9 , Issue.7 , pp. 241
    • Wahren, M.1
  • 44


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.