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Volumn , Issue 10, 2010, Pages 1741-1744

Practical one-pot syntheses of regioisomeric furan-fused pyridinones (and Quinolinones) from common precursors

Author keywords

Alkyne; Annulation; Cross coupling reaction; Furan; Microwave irradiation

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; IRRADIATION; ORGANIC POLLUTANTS;

EID: 77952067793     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218692     Document Type: Article
Times cited : (6)

References (18)
  • 14
    • 0001116319 scopus 로고
    • For mechanistic insights into acid-induced desilylations of silylacetylenes, see
    • For mechanistic insights into acid-induced desilylations of silylacetylenes, see:, Siehl H.-U, Kaufmann F.-P, Hori K, J. Am. Chem. Soc. 1992 114 9343
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9343
    • Siehl, H.-U.1    Kaufmann, F.-P.2    Hori, K.3
  • 15
    • 0035962679 scopus 로고    scopus 로고
    • For a previous synthesis of this compound see
    • For a previous synthesis of this compound see:, Bar G, Parsons A F., Thomas C B., Tetrahedron 2001 57 4719
    • (2001) Tetrahedron , vol.57 , pp. 4719
    • Bar, G.1    Parsons, A.F.2    Thomas, C.B.3
  • 16
    • 0017405222 scopus 로고
    • It is likely that, due to steric congestion, the methoxy methyl group in 2a is rotated out of the plane of the pyridinone ring resulting in decreased stability to nucleophilic attack with respect to 1a. This effect has often been invoked to explain the high degree of selectivity observed in the cleavage of polymethoxyarenes and is also expected to affect the rate of demethylation of benzo-fused 4-methoxypyridin-2-ones (quinolin-2-ones) like 3a. For leading references, see
    • It is likely that, due to steric congestion, the methoxy methyl group in 2a is rotated out of the plane of the pyridinone ring resulting in decreased stability to nucleophilic attack with respect to 1a. This effect has often been invoked to explain the high degree of selectivity observed in the cleavage of polymethoxyarenes and is also expected to affect the rate of demethylation of benzo-fused 4-methoxypyridin-2-ones (quinolin-2-ones) like 3a. For leading references, see:, Ahmad R, Saá J M., Cava M P., J. Org. Chem. 1977 42 1228
    • (1977) J. Org. Chem. , vol.42 , pp. 1228
    • Ahmad, R.1    Saá, J.M.2    Cava, M.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.