Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters

Martin G. Banwell; David W. Lupton; Xinghua Ma; Jens Renner; Magne O. Sydnes

doi:10.1021/ol0490375

Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters

Martin G. Banwell^*, David W. Lupton, Xinghua Ma, Jens Renner, Magne O. Sydnes

^*Corresponding author for this work

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Abstract

Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of β-halo-enals, -enones, or -esters readily affords the corresponding β-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl₃ in aqueous acetone.

Original language	English
Pages (from-to)	2741-2744
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	16
DOIs	https://doi.org/10.1021/ol0490375
Publication status	Published - 5 Aug 2004

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title = "Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters",

abstract = "Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of β-halo-enals, -enones, or -esters readily affords the corresponding β-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.",

author = "Banwell, {Martin G.} and Lupton, {David W.} and Xinghua Ma and Jens Renner and Sydnes, {Magne O.}",

year = "2004",

month = aug,

day = "5",

doi = "10.1021/ol0490375",

language = "English",

volume = "6",

pages = "2741--2744",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters. / Banwell, Martin G.; Lupton, David W.; Ma, Xinghua et al.
In: Organic Letters, Vol. 6, No. 16, 05.08.2004, p. 2741-2744.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters

AU - Banwell, Martin G.

AU - Lupton, David W.

AU - Ma, Xinghua

AU - Renner, Jens

AU - Sydnes, Magne O.

PY - 2004/8/5

Y1 - 2004/8/5

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AB - Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of β-halo-enals, -enones, or -esters readily affords the corresponding β-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.

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U2 - 10.1021/ol0490375

DO - 10.1021/ol0490375

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters

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