메뉴 건너뛰기




Volumn 48, Issue 49, 2007, Pages 8739-8742

Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions

Author keywords

Benzophenanthridine; Phenanthridine; Photostimulated reactions; SRN1

Indexed keywords

AMIDE; AMMONIA; AROMATIC AMINE; BENZOPHENANTHRIDINE DERIVATIVE; BENZYL CHLORIDE; HALIDE; PHENANTHRIDINE DERIVATIVE;

EID: 35748942574     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.009     Document Type: Article
Times cited : (31)

References (29)
  • 8
    • 77957094472 scopus 로고
    • Bross A. (Ed), Academic, New York, NY
    • Simanek V. In: Bross A. (Ed). The Alkaloids Vol. 26 (1985), Academic, New York, NY 185-240
    • (1985) The Alkaloids , vol.26 , pp. 185-240
    • Simanek, V.1
  • 9
    • 0002269682 scopus 로고
    • Bross A. (Ed), Academic, New York, NY
    • Suffiness W.M., and Gordell G.A. In: Bross A. (Ed). The Alkaloids Vol. 25 (1983), Academic, New York, NY 178-188
    • (1983) The Alkaloids , vol.25 , pp. 178-188
    • Suffiness, W.M.1    Gordell, G.A.2
  • 12
    • 0032815993 scopus 로고    scopus 로고
    • For a review of benzo[c]phenanthridine synthesis, see:
    • For a review of benzo[c]phenanthridine synthesis, see:. Ishikawa T., and Ishii H. Heterocycles 50 (1999) 627-638
    • (1999) Heterocycles , vol.50 , pp. 627-638
    • Ishikawa, T.1    Ishii, H.2
  • 18
    • 27444432809 scopus 로고    scopus 로고
    • Griesberck A.G., and Mattay J. (Eds), Marcel Dekker, New York
    • Rossi R.A. In: Griesberck A.G., and Mattay J. (Eds). Synthetic Organic Photochemistry Vol. 12, Chapter 15 (2005), Marcel Dekker, New York 495-527
    • (2005) Synthetic Organic Photochemistry , vol.12 Chapter 15 , pp. 495-527
    • Rossi, R.A.1
  • 24
    • 35748974054 scopus 로고    scopus 로고
    • Vogel's Textbook of Practical Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 1989; p 902.
  • 25
    • 35748973115 scopus 로고    scopus 로고
    • note
    • -{radical dot} is faster than the intermolecular reaction with radical traps.
  • 26
    • 0344887064 scopus 로고
    • 2 is 30.6 in DMSO), see: and references cited therein
    • 2 is 30.6 in DMSO), see:. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456-463 and references cited therein
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
    • Bordwell, F.G.1
  • 27
    • 35748941117 scopus 로고    scopus 로고
    • note
    • -{radical dot} (AM1/UHF method), this being the driving force of the coupling reaction.
  • 28
    • 35748948234 scopus 로고    scopus 로고
    • note
    • Although there are two non-equivalent ortho- positions to the amide group, the intramolecular reaction affords 11 regiospecifically. Ab initio calculations are in progress to inspect the electronic and geometric factors responsible for this regiochemistry.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.