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

被引：136

作者：

Banwell, MG ^{[1
]}

Lupton, DW ^{[1
]}

Ma, XH ^{[1
]}

Renner, J ^{[1
]}

Sydnes, MO ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol0490375

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-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.

引用

页码：2741 / 2744

页数：4

共 44 条

[1] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES
ALI, NM
MCKILLOP, A
MITCHELL, MB
REBELO, RA
WALLBANK, PJ
[J]. TETRAHEDRON, 1992, 48 (37) : 8117 - 8126
[2] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines
Amii, H
Kishikawa, Y
Uneyama, K
[J]. ORGANIC LETTERS, 2001, 3 (08) : 1109 - 1112
[3] A new green approach to the Friedlander synthesis of quinolines
Arcadi, A
Chiarini, M
Di Giuseppe, S
Marinelli, F
[J]. SYNLETT, 2003, (02) : 203 - 206
[4] ARNOLD Z, 1961, COLLECT CZECH CHEM C, V26, P3059
[5] REACTIONS OF TOLUENE-P-SULFONYL AZIDE WITH DERIVATIVES OF CYCLOHEPT-INDOLE AND CYCLO-OCT-INDOLE
BAILEY, AS
SEAGER, JF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (07): : 763 - 770
[6] Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[7] Synthesis of indoles via palladium[0]-mediated Ullmann cross-coupling of o-halonitroarenes with α-halo-enones or -enals
Banwell, MG
Kelly, BD
Kokas, OJ
Lupton, DW
[J]. ORGANIC LETTERS, 2003, 5 (14) : 2497 - 2500
[8] Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi
Banwell, MG
Edwards, AJ
Jolliffe, KA
Smith, JA
Hamel, E
Verdier-Pinard, P
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) : 296 - 305
[9] CONVERGENT ROUTES TO THE [1,3]DIOXOLO[4,5-J]PHENANTHRIDIN-6(5H)-ONE AND 2,3,4,4A-TETRAHYDRO[1,3]DIOXOLO[4,5-J]PHENANTHRIDIN-6(5H)-ONE NUCLEI - APPLICATION TO SYNTHESES OF THE AMARYLLIDACEAE ALKALOIDS CRINASIADINE, N-METHYLCRINASIADINE AND TRISPHAERIDINE
BANWELL, MG
COWDEN, CJ
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (12) : 2235 - 2254
[10] SYNTHESIS OF A METHYLSALICYLIC ACID-DERIVATIVE ISOLATED FROM OTHONNA-CYLINDRICA DC
BOHLMANN, F
FRITZ, G
[J]. CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (10): : 3371 - 3374

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