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Volumn 12, Issue 10, 2010, Pages 2406-2409

Synthesis of N-aryl and N-alkyl anthranilic acids via SNAr reaction of unprotected 2-fluoro- and 2-methoxybenzoic acids by lithioamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTHRANILIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; LITHIUM; ORGANOMETALLIC COMPOUND;

EID: 77952403302     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1007586     Document Type: Article
Times cited : (14)

References (49)
  • 7
    • 77952363177 scopus 로고    scopus 로고
    • Note for guidance on specification limits for residues of metal catalysts, 2002. The European Agency for the Evaluation of Medicinal Products Web site. (accessed April 21, 2010)
    • Note for guidance on specification limits for residues of metal catalysts, 2002. The European Agency for the Evaluation of Medicinal Products Web site. http://www.emea.europa.eu/pdfs/human/swp/444600en.pdf (accessed April 21, 2010).
  • 8
    • 77952385282 scopus 로고    scopus 로고
    • See, for instance
    • See, for instance
  • 14
    • 77952376167 scopus 로고    scopus 로고
    • note
    • Deprotection of 2-aminated aryloxazolines requires acidic conditions (3 M HCl, 12-24 h, reflux) which are not compatible with delicate structures. Yields do not exceed 70%, and in many instances the deprotection only leads to degradation products. See
  • 16
    • 77952378657 scopus 로고    scopus 로고
    • note
    • The reaction of 2-fluorobenzoic acid with s -BuLi and t -BuLi affords the the ipso -attack product arising out of substitution of the fluorine atom by the alkyl group
  • 18
    • 33644752654 scopus 로고    scopus 로고
    • Metalation reactions, recent references:
    • Metalation reactions, recent references: Nguyen, T. H.; Castanet, A.-S.; Mortier, J. Org. Lett. 2006, 8, 765-768
    • (2006) Org. Lett. , vol.8 , pp. 765-768
    • Nguyen, T.H.1    Castanet, A.-S.2    Mortier, J.3
  • 21
    • 77952379131 scopus 로고    scopus 로고
    • note
    • Two recent papers described LiHMDS-promoted coupling of primary and N -substituted anilines with 2-fluorobenzoic acid (or amide) to give N -arylanthranilic acids and N -arylanthranilamides
  • 24
    • 77952341947 scopus 로고    scopus 로고
    • note
    • x...). See
  • 25
    • 0342473735 scopus 로고    scopus 로고
    • A. C. Knipe, W. E. W., Ed.; John Wiley & Sons: UK
    • Crampton, M. R. Organic Reaction Mechanisms; A. C. Knipe, W. E. W., Ed.; John Wiley & Sons: UK, 2004; p 189.
    • (2004) Organic Reaction Mechanisms , pp. 189
    • Crampton, M.R.1
  • 26
    • 77952389152 scopus 로고    scopus 로고
    • note
    • Lithium arylamides have weaker nucleophilic strengths than lithium dialkylamines but are more stable at higher temperature (50-60 °C).
  • 27
    • 77952394137 scopus 로고    scopus 로고
    • note
    • 2 has been reported
  • 30
    • 77952339549 scopus 로고    scopus 로고
    • note
    • 2 gave only a slight decrease of yield of the substitution product 3.
  • 31
    • 77952331704 scopus 로고    scopus 로고
    • note
    • + forms a strong complex with the fluoro/methoxy group and the carboxylate. For the complex-induced proximity effect, CIPE, see
  • 33
    • 77952345327 scopus 로고    scopus 로고
    • note
    • 2 group enters from the side almost perpendicular to the aromatic ring (to the π cloud). This is consistent with the lack of steric inhibition to addition by large groups.
  • 34
    • 77952357644 scopus 로고    scopus 로고
    • note
    • The base and TMSCl were premixed prior to addition of the acid. The deprotonation which produces a small concentration of the trappable aryllithium 18 is sufficiently rapid to make the process competitive with reaction of the hindered base with the in situ electrophile (TMSCl). See ref 11b.
  • 35
    • 77952330268 scopus 로고    scopus 로고
    • Structure of 13 was confirmed by NOESY and HMBC (see Supporting Information)
    • Structure of 13 was confirmed by NOESY and HMBC (see Supporting Information).
  • 36
    • 77952395775 scopus 로고    scopus 로고
    • note
    • 2 (M = Li, K) group is a good director of ortho -metalation
  • 39
    • 77952364836 scopus 로고    scopus 로고
    • Wiley-Interscience: New York
    • Rappoport, Z. The Chemistry of Peroxides; Wiley-Interscience: New York, 2006; Vol. 2, part 1.
    • (2006) The Chemistry of Peroxides , vol.2 , Issue.PART 1
    • Rappoport, Z.1
  • 41
    • 77952381142 scopus 로고    scopus 로고
    • Observations of a similar rearrangement, leading to dioxindoles, have been reported
    • Observations of a similar rearrangement, leading to dioxindoles, have been reported
  • 43
    • 77952332179 scopus 로고    scopus 로고
    • note
    • In deoxygenated medium, the reaction of 2 with LiNMeBn (5 equiv) led to 5 (> 90%). It is assumed that the reduction step leading to 25 is the first irreversible step in the pathway.
  • 44
    • 77952348257 scopus 로고    scopus 로고
    • All new compounds gave correct analytical data. See Supporting Information
    • All new compounds gave correct analytical data. See Supporting Information.
  • 48
    • 77952406666 scopus 로고    scopus 로고
    • A patent application was filed
    • A patent application was filed


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.