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Volumn 64, Issue 27, 2008, Pages 6372-6376

First synthesis of 7-amido-[1,2,4]triazolo[1,5-a]pyrimidines using halogen-metal exchange

Author keywords

[No Author keywords available]

Indexed keywords

7 AMIDO [1,2,4]TRIAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; AMIDE; CARBAMOYL CHLORIDE DERIVATIVE; CHLORIDE; CYANIDE; ESTER DERIVATIVE; HALOGEN; KETONE DERIVATIVE; METAL; PYRIMIDINE DERIVATIVE;

EID: 44349095722     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.084     Document Type: Article
Times cited : (14)

References (41)
  • 1
    • 44349094349 scopus 로고    scopus 로고
    • For some recent reviews on crop protection chemistry see:
    • For some recent reviews on crop protection chemistry see:
  • 10
    • 10244233277 scopus 로고
    • Baker D.R., Fenyes J.G., and Steffens J.J. (Eds), American Chemical Society, Washington, DC
    • Costales M.J., Kleschick W.A., and Gerwick B.C. In: Baker D.R., Fenyes J.G., and Steffens J.J. (Eds). Synthesis and Chemistry of Agrochemicals III. ACS Symposium Series 504 (1992), American Chemical Society, Washington, DC 26-33
    • (1992) ACS Symposium Series 504 , pp. 26-33
    • Costales, M.J.1    Kleschick, W.A.2    Gerwick, B.C.3
  • 15
    • 44349127903 scopus 로고    scopus 로고
    • note
    • 191 Patent applications on triazolopyrimidine fungicides have been published by six different companies between 1993 and 2007.
  • 16
    • 44349150460 scopus 로고    scopus 로고
    • Pees, K.J.; Albert, G. (Shell) European Patent Application 550113, 1993
    • Pees, K.J.; Albert, G. (Shell) European Patent Application 550113, 1993
  • 17
    • 27944435091 scopus 로고
    • ( )
    • (. Chem. Abstr. 119 (1993) 271190 )
    • (1993) Chem. Abstr. , vol.119 , pp. 271190
  • 20
    • 44349194955 scopus 로고    scopus 로고
    • Jelich, K.; Kraemer, W.; Santel, H. J.; Schmidt, R. R.; Strang, H; Bayer A.-G. DE 3640155, 1988;
    • Jelich, K.; Kraemer, W.; Santel, H. J.; Schmidt, R. R.; Strang, H; Bayer A.-G. DE 3640155, 1988;
  • 21
    • 44349135742 scopus 로고    scopus 로고
    • Jelich, K.; Santel, H. J.; Schmidt, R. R; Bayer A.-G. DE3534651, 1987.
    • Jelich, K.; Santel, H. J.; Schmidt, R. R; Bayer A.-G. DE3534651, 1987.
  • 22
    • 44349188051 scopus 로고    scopus 로고
    • Compound 7 is prepared according to the following patent of BASF: Pees, K.-J.; Albert, G. U.S. Patent 6,297,251, 2001 or Pees, K.-J.; Albert, G. U.S. Patent 6,117,876, 2000; Pees, K.-J; Albert, G. WO9846607, 1998.
    • Compound 7 is prepared according to the following patent of BASF: Pees, K.-J.; Albert, G. U.S. Patent 6,297,251, 2001 or Pees, K.-J.; Albert, G. U.S. Patent 6,117,876, 2000; Pees, K.-J; Albert, G. WO9846607, 1998.
  • 23
    • 84959947882 scopus 로고
    • and references cited therein
    • Minisci F. Synthesis 1 (1973) 1 and references cited therein
    • (1973) Synthesis , vol.1 , pp. 1
    • Minisci, F.1
  • 24
    • 44349194382 scopus 로고    scopus 로고
    • note
    • 4, MeOH, reflux, 5 h.
  • 25
    • 44349103087 scopus 로고    scopus 로고
    • Blettner, C.; Tormo, J.; Mueller, B.; Gewehr, M.; Grammenos, W.; Grote, T.; Huenger, U.; Rheinheimer, J.; Schaefer, P.; Schieweck, F.; Schwoegler, A.; Wagner, O.; Speakman, J.-B.; Jabs, T.; Strathmann, S.; Schoefl, U.; Scherer, M.; Stierl, R. WO2006034848, 2006.
    • Blettner, C.; Tormo, J.; Mueller, B.; Gewehr, M.; Grammenos, W.; Grote, T.; Huenger, U.; Rheinheimer, J.; Schaefer, P.; Schieweck, F.; Schwoegler, A.; Wagner, O.; Speakman, J.-B.; Jabs, T.; Strathmann, S.; Schoefl, U.; Scherer, M.; Stierl, R. WO2006034848, 2006.
  • 28
    • 44349092150 scopus 로고    scopus 로고
    • Crowley, P.; Syngenta A. G. Unpublished results.
    • Crowley, P.; Syngenta A. G. Unpublished results.
  • 31
    • 44349133396 scopus 로고    scopus 로고
    • note
    • The standard procedure was modified and the electrophile introduced before NaH to trap immediately the formed anion.
  • 32
    • 44349161181 scopus 로고    scopus 로고
    • note
    • The monoanion of the amide 10 is not stable: a mixture of 10 in THF with 1 equiv of NaH at 0 °C for 10 min gave as only product, the reduced compound 6 (8% yield).
  • 40
    • 44349120631 scopus 로고    scopus 로고
    • The low yield could be explained by the reactivity of the t-BuLi toward DME, which is known in the literature:
    • The low yield could be explained by the reactivity of the t-BuLi toward DME, which is known in the literature:. Stanetty P., and Milhovilovic M.D. J. Org. Chem. 62 (1997) 1541
    • (1997) J. Org. Chem. , vol.62 , pp. 1541
    • Stanetty, P.1    Milhovilovic, M.D.2
  • 41
    • 29344432351 scopus 로고    scopus 로고
    • 2MgCl·LiCl complex was tried for this exchange, we isolated only 14:
    • 2MgCl·LiCl complex was tried for this exchange, we isolated only 14:. Krasovskiy A., Straub B.F., and Knochel P. Angew. Chem., Int. Ed. 45 (2006) 159
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 159
    • Krasovskiy, A.1    Straub, B.F.2    Knochel, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.