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Volumn 47, Issue 41, 2006, Pages 7317-7322

One-pot synthesis of 2-substituted furo[3,2-c]quinolines via tandem coupling-cyclization under Pd/C-copper catalysis

Author keywords

3 Iodo 1H quinolin 4 ones; Furo 3,2 c quinolines; Palladium catalyst; Terminal alkynes

Indexed keywords

3 IODO 1H QUINOLIN 4 ONE DERIVATIVE; ALKYL GROUP; ALKYNE DERIVATIVE; CARBON; COPPER COMPLEX; FURO[3,2 C]QUINOLINE DERIVATIVE; NITROGEN; PALLADIUM; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33748309418     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.025     Document Type: Article
Times cited : (44)

References (75)
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    • For Pd-mediated synthesis of furo[2,3-b]pyridones from 3-alkynylpyridones, see:. Bossharth E., Desbordes P., Monteiro N., and Balme G. Org. Lett. 5 (2003) 2441-2444
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    • For the preparation of 6-fluoro-4-oxo-1,4-dihydroquinoline-2-carboxylic acid methyl ester 1b, see:
    • For the preparation of 6-fluoro-4-oxo-1,4-dihydroquinoline-2-carboxylic acid methyl ester 1b, see:. Edmont D., Rocher R., Plisson C., and Chenault J. Bioorg. Med. Chem. Lett. 10 (2000) 1831-1834
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    • To a solution of appropriately substituted quinolin-4-one (1, 4.52 mmol) in acetonitrile (25 mL) was added ceric ammonium nitrate (0.248 g, 0.45 mmol) followed by iodine (0.631 g, 4.97 mmol). The mixture was stirred at 70-80 °C under nitrogen for 3-8 h. After completion of the reaction, the mixture was cooled to room temperature and treated with an ice-cold aqueous solution of sodium thiosulfate with stirring. The resulting precipitated solid was filtered to afford the desired product.
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    • 3CN, gradient (T/%B) 0/40, 5/40, 20/80, 25/80, 30/40, 35/40, flow rate: 1.0 mL/min, UV 254 nm, retention time 12.4 min.
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    • Cu(I) in DMF has been reported as an efficient catalytic system for a similar cyclization process; see for example:
    • Cu(I) in DMF has been reported as an efficient catalytic system for a similar cyclization process; see for example:. Patil N.T., Wu H., and Yamamoto Y. J. Org. Chem. 70 (2005) 4531-4534
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    • note
    • An alternative pathway involving activation of the carbonyl group through the coordination of Cu(I) to the carbonyl oxygen and the π-bond of the alkyne may also facilitate the intramolecular cyclization process, see Ref. 32.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.