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Volumn 48, Issue 19, 2007, Pages 3359-3362

A new approach to the 1,10-phenanthroline core

Author keywords

1,10 Phenanthroline; Intramolecular coupling; Nitrogen heterocycles; Ullmann reaction

Indexed keywords

1,10 PHENANTHROLINE; ALDEHYDE DERIVATIVE; ETHYLENE DERIVATIVE; PHOSPHONIUM DERIVATIVE; PYRIDINE DERIVATIVE;

EID: 34147134905     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.073     Document Type: Article
Times cited : (24)

References (36)
  • 6
    • 0001827606 scopus 로고
    • Wilkinson G., Gillard R.D., and McCleverty J.A. (Eds), Pergamon Press, Oxford
    • Reedijk J. In: Wilkinson G., Gillard R.D., and McCleverty J.A. (Eds). Comprehensive Coordination Chemistry Vol. 2 (1987), Pergamon Press, Oxford 73-98
    • (1987) Comprehensive Coordination Chemistry , vol.2 , pp. 73-98
    • Reedijk, J.1
  • 26
    • 0842305971 scopus 로고    scopus 로고
    • For a leading reference on the coupling of pyridine by the Ullmann reaction, see:
    • For a leading reference on the coupling of pyridine by the Ullmann reaction, see:. Newkome G.R., Patri A.K., Holder E., and Schubert U.S. Eur. J. Org. Chem. (2004) 235
    • (2004) Eur. J. Org. Chem. , pp. 235
    • Newkome, G.R.1    Patri, A.K.2    Holder, E.3    Schubert, U.S.4
  • 31
    • 34147119316 scopus 로고    scopus 로고
    • For a related procedure, see: Ref. 7.
  • 32
    • 34147160432 scopus 로고    scopus 로고
    • note
    • 3): δ 158.6, 148.3, 147.1, 146.0, 144.3, 135.6, 131.2, 129.7, 127.5, 127.2, 126.7, 126.5, 125.6, 125.3, 121.9, 25.6, 19.1.
  • 33
    • 34147104185 scopus 로고    scopus 로고
    • note
    • The number of steps needed to obtain phenanthrolines 1a-f and the related overall yield from commercially available pyridine derivatives are reported. Phenanthroline 1a was obtained in three steps (60%) from 2-bromonicotinaldehyde 6a and in four steps (41%) from 2-bromo-3-methylpyridine. Phenanthroline 1b was obtained in four steps (40%) from 2-hydroxy-6-methylnicotinonitrile and in four steps (46%) from 2-bromo-3-methylpyridine. Phenanthroline 1c was obtained in four steps (31%) and in seven steps (16%) from 2-hydroxy-6-methylnicotinonitrile (this pyridine is the common starting material for both bromoaldehyde 6b and phosphonium salt 7b). Phenanthroline 1d was obtained in four steps (25%) from 2-hydroxy-4,6-dimethylnicotinonitrile and in four steps (37%) from 2-bromo-3-methylpyridine. Phenanthroline 1e was obtained in four steps (19%) and from 2-hydroxy-6-methylnicotinonitrile and in four steps (21%) from 2-chloroquinoline-3-carbaldehyde. Phenanthroline 1f was obtained in four steps (5%) from 2-hydroxy-4,6-dimethylnicotinonitrile and in four steps (7%) from 2-chloroquinoline-3-carbaldehyde.


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