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Volumn 2, Issue 3, 2009, Pages 218-220

Electrophilic activation of aldehydes "on water": A facile route to dipyrromethanes

Author keywords

Aldehydes; Heterocycles; Nitrogen; Nucleophilic addition

Indexed keywords

ALDEHYDE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; DIPYRROMETHANE; PYRROLE DERIVATIVE; WATER;

EID: 67649827370     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.200900023     Document Type: Article
Times cited : (16)

References (51)
  • 24
    • 34848868730 scopus 로고    scopus 로고
    • for the use of alkylthio units as protecting groups in dipyrromethane synthesis, see
    • s) D. Kiper Dogutan, S. Huma, H. Zaidi, P. Thamyongkit, J. S. Lindsey, J. Org. Chem. 2007, 72, 7701; for the use of alkylthio units as protecting groups in dipyrromethane synthesis, see.
    • (2007) J. Org. Chem. , vol.72 , pp. 7701
    • Kiper Dogutan, D.1    Huma, S.2    Zaidi, H.3    Thamyongkit, P.4    Lindsey, J.S.5
  • 28
    • 20344388819 scopus 로고    scopus 로고
    • For a discussion of reactions performed in water, see also
    • Angew. Chem. Int. Ed. 2005, 44, 3275. For a discussion of reactions performed in water, see also.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 275
  • 38
    • 0346456931 scopus 로고    scopus 로고
    • For other interesting reactions on water, see M.C., Pirrung, K. Das Sarma
    • For other interesting reactions on water, see: a) M. C. Pirrung, K. Das Sarma, J. Am. Chem. Soc. 2004, 126, 444.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 444
  • 42
    • 56449125505 scopus 로고    scopus 로고
    • Pirrung, co-workers recently proposed an alternative explanation for on water acceleration, see
    • Pirrung and co-workers recently proposed an alternative explanation for on water acceleration; see: M. C. Pirrung, K. D. Sarma, J. Wang, J. Org. Chem. 2008, 73, 8723.
    • (2008) J. Org. Chem. , vol.73 , pp. 8723
    • Pirrung, M.C.1    Sarma, K.D.2    Wang, J.3
  • 43
    • 70449121183 scopus 로고    scopus 로고
    • For Lewis acid catalyst free electrophilic alkylation in 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol, see, Angew, Chem., Int., Ed., 2008 50 9739
    • For Lewis acid catalyst free electrophilic alkylation in 1,1,1,3,3,3-hexafluoro-2-propanol, see: a) M. O. Ratnikov, V. V. Tumanov, W. A. Smit, Angew. Chem. 2008, 120, 9885; Angew. Chem. Int. Ed. 2008, 50, 9739;.
    • (2008) Angew. Chem. , vol.120 , pp. 9885
    • Ratnikov, M.O.1    Tumanov, V.V.2    Smit, W.A.3
  • 45
    • 53749100577 scopus 로고    scopus 로고
    • For the electrophilicity of pyrrole see: For a related article considering the reaction of electrophiles with indole, see
    • For the electrophilicity of pyrrole, see: a) T. A. Nigst, M. Westermaier, A. R. Ofial, H. Mayr, Eur. J. Org. Chem. 2008, 2369. For a related article considering the reaction of electrophiles with indole, see.
    • (2008) J. Org. Chem. , pp. 2369
    • Nigst, T.A.1    Westermaier, M.2    Ofial, A.R.3    Mayr, E.4
  • 47
    • 85021032593 scopus 로고    scopus 로고
    • note
    • The pH was measured with a glass electrode applied in the water phase.
  • 48
    • 55249095404 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008 47, 2849; Angew. Chem. Int. Ed. 2008, 47, 2849
    • N. Shapiro, A. Vigalok, Angew. Chem. 2008, 120, 2891; Angew. Chem. Int. Ed. 2008, 47, 2849; Angew. Chem. Int. Ed. 2008, 47, 2849.
    • (2008) Angew. Chem. , vol.120 , pp. 2891
    • Shapiro, N.1    Vigalok, A.2
  • 49
    • 85020985536 scopus 로고    scopus 로고
    • note
    • In the presence of buffers, the reaction is slowed down. These experiments show that acidic pH (3.8) is not crucial for the reaction.
  • 50
    • 0034615954 scopus 로고    scopus 로고
    • The reactions were performed with an aldehyde/pyrrole ratio of 1:14 at 85-140 °C, see
    • The reactions were performed with an aldehyde/pyrrole ratio of 1:14 at 85-140 °C; see: D. Gryko, J. S. Lindsey, J. Org. Chem. 2000, 65, 2249.
    • (2000) J. Org. Chem. , vol.65 , pp. 2249
    • Gryko, D.1    Lindsey, J.S.2
  • 51
    • 85020948345 scopus 로고    scopus 로고
    • note
    • A patent application in the name of the University of Bologna has been filed relating to the method disclosed herein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.