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Volumn 51, Issue 50, 2010, Pages 6535-6538

Application of biphasic reaction procedure using ferric chloride dissolved in an imidazolium salt and benzotrifluoride (FeIm-BTF procedure) to aza-Prins cyclization reaction

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1 BUTYL 3 METHYLIMIDAZOLIUM TETRACHLOROFERRATE; ALDEHYDE DERIVATIVE; ALIPHATIC COMPOUND; AMINE; AROMATIC COMPOUND; BENZALDEHYDE; BENZOTRIFLUORIDE; DICHLOROMETHANE; FERRIC CHLORIDE; FLUORIDE; IMIDAZOLE DERIVATIVE; N TOSYL 3 BUTENYLAMINE; N TOSYL 4 CHLORO 2 PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 78650244897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.018     Document Type: Article
Times cited : (17)

References (56)
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    • To the best of our knowledge, BTF has never been employed as a solvent for aza-Prins cyclization while some examples of aza-Prlns cyclization in ionic liquids are reported (a) Kishi, Y.; Nagura, H.; Inagi, S.; Fuchigami, T. Chem. Commun. 2008, 3876-3878
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    • note
    • 7a and thus characterization of the piperidlnes 3 obtained and determination of their relative stereochemistry were performed by the comparison of their spectral data with those of the reported compounds.
  • 42
    • 77954856171 scopus 로고    scopus 로고
    • Mixing of metal salts with imidazolium salts is expected to undergo ion pair exchange. These processes may influence the Lewis acidic property of metal ions. Related review Lee, J. W.; Shin, J. Y.; Chun, Y. S.; Jang, H. B.; Song, C. E.; Lee, S. G. Acc. Chem. Res. 2010, 43, 985-994.
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    • Lee, J.W.1    Shin, J.Y.2    Chun, Y.S.3    Jang, H.B.4    Song, C.E.5    Lee, S.G.6
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    • note
    • 4. The residue obtained after concentration was purified by silica-gel column chromatography (EtOAc/n-Hexane solvent systems), and then subjected to TLC (EtOAc/n-Hexane solvent systems).
  • 54
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    • Independent reviewers suggested the possibility of the formation of byproducts such as tetrahydropyridines, pyrrolidines, and Tishchenko type products from aldehydes particularly when 3 were obtained in low yields. At present, the formation of such compounds has not been confirmed
    • Independent reviewers suggested the possibility of the formation of byproducts such as tetrahydropyridines, pyrrolidines, and Tishchenko type products from aldehydes particularly when 3 were obtained in low yields. At present, the formation of such compounds has not been confirmed.
  • 55
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    • Actual roles of BTF and imidazolium salts have not been fully understood yet. Significant progress of the piperidine yields might be ascribed to the liquid phase iron reagents while BTF is particularly beneficial for the separation step
    • Actual roles of BTF and imidazolium salts have not been fully understood yet. Significant progress of the piperidine yields might be ascribed to the liquid phase iron reagents while BTF is particularly beneficial for the separation step.
  • 56
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    • 4NCl. If this devised procedure works, then imidazolium layer might be reusable, which would be certainly the future subject to investigate
    • 4NCl. If this devised procedure works, then imidazolium layer might be reusable, which would be certainly the future subject to investigate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.