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Volumn 67, Issue 19, 2011, Pages 3457-3463

α-Dimethylaminomethylenation-induced Houben-Hoesch-type cyclization of cyanoacetanilides: A practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)- ones

Author keywords

Electrophilic aromatic substitution; Nitrile; Triflic anhydride; Trifluoroacetic anhydride; Vilsmeier reagent

Indexed keywords

3 FORMYL 4 HYDROXYQUINOLIN 2(1H) ONE; ACETANILIDE DERIVATIVE; AMINE; CARBENE; FORMIC ACID DERIVATIVE; N,N DIMETHYLFORMAMIDE; QUINOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 79955048911     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.040     Document Type: Article
Times cited : (17)

References (39)
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    • 2 (or even in pyridine).
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    • 2O is ca. 57000 JPY/mol (Aldrich, 2010).
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    • 13C NMR spectra; the C2 atoms of 2a-q, having stronger electron-donating substituents (X), were shielded (71.3-77.0 ppm) relative to those of 2r and 2s (95.0 and 89.1 ppm, respectively). The CN carbon atoms of 2a-q were deshielded (116.9-119.7 ppm) than those of 2r and 2s (113.2 and 112.0 ppm, respectively)
    • 13C NMR spectra; the C2 atoms of 2a-q, having stronger electron-donating substituents (X), were shielded (71.3-77.0 ppm) relative to those of 2r and 2s (95.0 and 89.1 ppm, respectively). The CN carbon atoms of 2a-q were deshielded (116.9-119.7 ppm) than those of 2r and 2s (113.2 and 112.0 ppm, respectively)
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    • 4a (Eq. 4)
    • 4a (Eq. 4).
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    • To detect the intermediate, such as, C′, we carried out the NMR experiments using piperidine-derived acrylamide with TFAA and DMF. However, we could not observe the cation species, such as C′ on the NMR time scale, see the Supplementary data
    • To detect the intermediate, such as, C′, we carried out the NMR experiments using piperidine-derived acrylamide with TFAA and DMF. However, we could not observe the cation species, such as C′ on the NMR time scale, see the Supplementary data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.