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Volumn 60, Issue 10, 2004, Pages 2181-2186

Regioselectivities in deprotonation of 2-(4-chloro-2-pyridyl)benzoic acid and corresponding ester and amide

Author keywords

Mechanism; Metallation; Onychine; Pyridines

Indexed keywords

1 CHLORO 4 AZAFLUORENONE; 2 (4 CHLORO 2 PYRIDYL)BENZOATE; 2 (4 CHLORO 2 PYRIDYL)BENZOIC ACID; ALKALOID DERIVATIVE; ANTIFUNGAL AGENT; BENZAMIDE DERIVATIVE; BENZOIC ACID DERIVATIVE; FLUORENONE DERIVATIVE; N,N DIISOPROPYL 2 (4 CHLORO 2 PYRIDYL)BENZAMIDE; ONYCHINE; UNCLASSIFIED DRUG;

EID: 1242306180     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.050     Document Type: Article
Times cited : (15)

References (53)
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    • Note that functionalization at both C6 and C5′ was observed using a large excess of LTMP, and chlorotrimethylsilane as an in situ trap
    • Note that functionalization at both C6 and C5′ was observed using a large excess of LTMP, and chlorotrimethylsilane as an in situ trap.
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    • The spectra were recorded with a ReactIR™ 4000 fitted with an immersible DiComp ATR probe (ASI Applied Systems, Mettler Toledo)
    • The spectra were recorded with a ReactIR™ 4000 fitted with an immersible DiComp ATR probe (ASI Applied Systems, Mettler Toledo).
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    • Deprotonation of N,N-diisopropylbenzamide was often achieved using alkyllithiums: see Ref. 1e. The reaction was suggested to proceed by a two-step mechanism of largely reversible initial complexation between the substrate and the organolithium reagent, which is followed by hydrogen transfer to the organolithium reagent
    • Deprotonation of N,N-diisopropylbenzamide was often achieved using alkyllithiums: see Ref. 1e. The reaction was suggested to proceed by a two-step mechanism of largely reversible initial complexation between the substrate and the organolithium reagent, which is followed by hydrogen transfer to the organolithium reagent.
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    • In situ infrared spectroscopy showed incomplete deprotonation when fewer equivalents of LTMP were used. Note that lithiation of 4-chloropyridine was achieved using 1 equiv of LDA in THF at -75 °C:
    • In situ infrared spectroscopy showed incomplete deprotonation when fewer equivalents of LTMP were used. Note that lithiation of 4-chloropyridine was achieved using 1 equiv of LDA in THF at -75 °C: Gribble G.W., Saulnier M.G. Tetrahedron Lett. 21:1980;4137-4140.
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    • See for example: the deprotonation is sufficiently rapid to make this process competitive in rate with the reaction of the hindered base with the in situ electrophile
    • See for example: Imahori T., Uchiyama M., Sakamoto T., Kondo Y. Chem. Commun. 23:2001;2450-2451. the deprotonation is sufficiently rapid to make this process competitive in rate with the reaction of the hindered base with the in situ electrophile.
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    • Concerning cross-couplings of primary alkylboronic acids with aryl halides, see: Molander G.A., Yun C.-S. Tetrahedron. 58:2002;1465-1470.
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    • Onychine was first isolated from the Brazilian Annonaceae species (Onychopetalum amazonicum, Guatteria dielsiana) in 1976 and was shown to have anticandidal activity: (a)
    • Onychine was first isolated from the Brazilian Annonaceae species (Onychopetalum amazonicum, Guatteria dielsiana) in 1976 and was shown to have anticandidal activity: (a) De Almeida M.E.L., Braz Filho R., von Bülow V., Gottlieb O.R., Maia J.G.S. Phytochemistry. 15:1976;1186-1187.
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    • note
    • In the step from 5 to 10 , the recovered amide 5 was indeed deuterated at C5′
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    • Concerning the deprotonation of methylpyridines, see: (a)
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.