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Volumn 71, Issue 16, 2006, Pages 6291-6294

A route to regioselectively functionalized carbazoles, dibenzofurans, and dibenzothiophenes through anionic cyclization of benzyne-tethered aryllithiums

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; NITROGEN COMPOUNDS; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 33746893067     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060911c     Document Type: Article
Times cited : (74)

References (62)
  • 2
    • 0040418708 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Chapter 2.3
    • (b) Kessar, V. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 2.3.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Kessar, V.S.1
  • 22
    • 0002777371 scopus 로고
    • Introduced independently by Huisgen and Bunnet: (a) Huisgen, R.; Sauer, J. Angew. Chem. 1960, 72, 91-108.
    • (1960) Angew. Chem. , vol.72 , pp. 91-108
    • Huisgen, R.1    Sauer, J.2
  • 28
    • 0001068611 scopus 로고
    • (a) Iwao, M. J. Org. Chem. 1990, 55, 3622-3627.
    • (1990) Org. Chem. , vol.55 , pp. 3622-3627
    • Iwao, M.J.1
  • 41
    • 7044223075 scopus 로고    scopus 로고
    • Larock and Liu have reported a two-step synthesis of carbazoles and dibenzofurans by the cross-coupling of o-iodoanilines or phenols with arynes, followed by Pd-catalyzed intramolecular cyclization: Liu, Z.; Larock, R. C. Org. Lett. 2004, 6, 3739-3741.
    • (2004) Org. Lett. , vol.6 , pp. 3739-3741
    • Liu, Z.1    Larock, R.C.2
  • 46
    • 33746872836 scopus 로고    scopus 로고
    • (b) Jones, K. Sci. Synth. 2001, 10, 131-153.
    • (2001) Sci. Synth. , vol.10 , pp. 131-153
    • Jones, K.1
  • 53
    • 33746894443 scopus 로고    scopus 로고
    • note
    • Secondary N-alkyl-2-fluoroanilines were prepared by alkylation of 2-fluoroaniline; see ref 10b. Although in lower yield, amine 1a could also be prepared by treatment of the lithium amide of N-methyl-2-fluoroaniline with o-chloronitrobenzene in THF at reflux.
  • 56
    • 33746909007 scopus 로고    scopus 로고
    • note
    • Treatment of N-(2-bromophenyl)-2-fluoroaniline with 4.3 equiv of t-BuLi only gave rise to deprotonation and bromine-lithium exchange. Subsequent cyclization was not observed.
  • 57
    • 0003414262 scopus 로고
    • Windholz, M., Budavari, S., Blumetti, R. F., Otterbein, E. S., Eds. Merck & Co., Inc.: Rathway, NJ
    • (a) Windholz, M., Budavari, S., Blumetti, R. F., Otterbein, E. S., Eds. The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals; Merck & Co., Inc.: Rathway, NJ, 1983.
    • (1983) The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals
  • 59
    • 0002487057 scopus 로고
    • Katritzky, A. R., Ed.; Academic Press: Orlando, FL
    • Joule, J. A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL, 1984; Vol. 35, pp 83-198.
    • (1984) Advances in Heterocyclic Chemistry , vol.35 , pp. 83-198
    • Joule, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.