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Volumn , Issue 10, 2006, Pages 1590-1598

Syntheses of ring-fluorinated isoquinolines and quinolines via intramolecular substitution: Cyclization of 1,1-difluoro-1-alkenes bearing a sulfonamide moiety

Author keywords

Desulfonylation; Fluoroalkene; Fluoroisoquinoline; Fluoroquinoline; Intramolecular substitution

Indexed keywords

MOLECULAR ORIENTATION; SODIUM COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 33744470613     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926458     Document Type: Article
Times cited : (30)

References (51)
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  • 4
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  • 27
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    • Classical Baltz-Schiemann (fluorodediazotization) and Halex (halogen exchange) approaches are still extensively used: Chemistry of Organic Fluorine Compounds II; Hudlicky, M.; Pavlath, A. E., Eds.; American Chemical Society: Washington, DC, 1995.
    • (1995) Chemistry of Organic Fluorine Compounds II
  • 30
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    • For the synthesis of quinolines selectively fluorinated on their heterocyclic ring, see: (a) Ondi, L.; Volle, J.-N.; Schlosser, M. Tetrahedron 2005, 61, 717.
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  • 40
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    • and references cited therein
    • and references cited therein. For desulfonylation on nitrogens to quinolines, see: (c) Kim, J. N.; Chunh, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209; and references cited therein.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6209
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  • 43
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    • N2′ reaction, when the vinylic substituent R is a silyl or an aryl group. See: (a) Ichikawa, J.; Fukui, H.; Ishibashi, Y. J. Org. Chem. 2003, 68, 7800.
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  • 47
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    • note
    • Anilide 7c (R = H) hardly gave dihydroquinoline 10c (R = H) on teatment with NaH, which suggests that 10c was formed via desilylation of 10b.
  • 48
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    • note
    • For the synthesis of 3-fluoroquinolines starting from (2,2-difluorovinyl)benzene substrates on the basis of the intramolecular substitution concept, see: Refs. 4e, 5b, 12b, and 12c. 1599-1612


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.