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Volumn 73, Issue 3, 2008, Pages 1169-1172

Reaction of aldimine anions with vinamidinium chloride: Three-component access to 3-alkylpyridines and 3-alkylpyridinium salts and access to 2-alkyl glutaconaldehyde derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLAMINOPENTADIENIMINE DERIVATIVES; ALKYLPYRIDINES; AMMONIUM ACETATE; VINAMIDINIUM CHLORIDE;

EID: 38849207828     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702311k     Document Type: Article
Times cited : (22)

References (20)
  • 2
    • 21244490314 scopus 로고    scopus 로고
    • For a recent review on pyridines and pyridinium salts syntheses, see:, Black, D. StC, Ed, Georg Thieme Verlag: Stuttgart, New York
    • For a recent review on pyridines and pyridinium salts syntheses, see: Spitzner, D. In Science of Synthesis; Black, D. StC., Ed.; Georg Thieme Verlag: Stuttgart, New York, 2005; Vol. 15, pp 11-284.
    • (2005) Science of Synthesis , vol.15 , pp. 11-284
    • Spitzner, D.1
  • 14
    • 38849134502 scopus 로고    scopus 로고
    • The use of a tertiary amine in these reactions is recommended (see refs 6 and 7). Its role can be to facilitate elimination of diethylamine from the primary adduct of the reaction, but this was not proven yet.
    • The use of a tertiary amine in these reactions is recommended (see refs 6 and 7). Its role can be to facilitate elimination of diethylamine from the primary adduct of the reaction, but this was not proven yet.
  • 16
    • 85069754511 scopus 로고    scopus 로고
    • For a review on the synthesis and reactions of glutaconaldehyde and the corresponding amino derivatives aminopentadienals, see: Becher, J. Synthesis 1980, 589-612
    • (b) For a review on the synthesis and reactions of glutaconaldehyde and the corresponding amino derivatives (aminopentadienals), see: Becher, J. Synthesis 1980, 589-612.
  • 17
    • 13444267332 scopus 로고    scopus 로고
    • A similar reaction was reported starting from a diaryl ketone and using a chlorovinamidinium salt. The chloropyridine obtained in 35% yield was further reduced to give a 2,3-diarylpyridine: Simoni, D.; Grisolia, G.; Giannini, G.; Roberti, M.; Rondanin, R.; Piccagli, L.; Barrichello, R.; Rossi, M.; Romagnoli, R.; Invidiata, F. P.; Grimaudo, S.; Jung, M. K.; Hamel, E.; Gebbia, N.; Crosta, L.; Abbadessa, V.; Di Cristina, A.; Dusonchet, L.; Meli, M.; Tolomeo, M. J. Med. Chem. 2005, 48, 723-736.
    • A similar reaction was reported starting from a diaryl ketone and using a chlorovinamidinium salt. The chloropyridine obtained in 35% yield was further reduced to give a 2,3-diarylpyridine: Simoni, D.; Grisolia, G.; Giannini, G.; Roberti, M.; Rondanin, R.; Piccagli, L.; Barrichello, R.; Rossi, M.; Romagnoli, R.; Invidiata, F. P.; Grimaudo, S.; Jung, M. K.; Hamel, E.; Gebbia, N.; Crosta, L.; Abbadessa, V.; Di Cristina, A.; Dusonchet, L.; Meli, M.; Tolomeo, M. J. Med. Chem. 2005, 48, 723-736.
  • 18
    • 38849113572 scopus 로고    scopus 로고
    • Free glutacondialdehyde derivatives are very unstable intermediates (glutaconaldehyde is stable for only ∼30 mn at ∼-70°C (see ref 10b) or prone to dimerization see ref 5
    • Free glutacondialdehyde derivatives are very unstable intermediates (glutaconaldehyde is stable for only ∼30 mn at ∼-70°C (see ref 10b) or prone to dimerization (see ref 5)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.