Practical One-Pot Syntheses of Regioisomeric Furan-Fused Pyridinones (and Quinolinones) from Common Precursors

被引：4

作者：

Delaunay, Thierry ^{[1
]}

Conreaux, David ^{[1
]}

Bossharth, Emmanuel ^{[1
]}

Desbordes, Philippe ^{[2
]}

Monteiro, Nuno ^{[1
]}

Balme, Genevieve ^{[1
]}

机构：

[1] Univ Lyon 1, ESCPE Lyon, CNRS, ICBMS,UMR 5246, F-69622 Villeurbanne, France

[2] Bayer Crop Sci, F-69623 Lyon 09, France

来源：

SYNTHESIS-STUTTGART | 2010年 / 10期

关键词：

annulation; furan; alkyne; cross-coupling reaction; microwave irradiation; DEMETHYLATION; FUROQUINOLINONES;

D O I：

10.1055/s-0029-1218692

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Alkynyl-4-methoxypyridin-2(1H)-ones undergo cyclization via divergent pathways when heated in acetic acid or triethylamine as reagent-solvent under microwave irradiation to furnish selectively furo[2,3-b]pyridin-4-ones or their regioisomeric furo[3,2-c]pyridin-4-ones, respectively. The same strategy applies to the synthesis of furoquinolinones.

引用

页码：1741 / 1744

页数：4

共 19 条

[1] REGIOSELECTIVE O-DEMETHYLATION IN APORPHINE ALKALOID SERIES [J].

AHMAD, R ;

SAA, JM ;

CAVA, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) :1228-1230

[2] A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization [J].

Aillaud, I ;

Bossharth, E ;

Conreaux, D ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2006, 8 (06) :1113-1116

[3] Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids [J].

Bar, G ;

Parsons, AF ;

Thomas, CB .

TETRAHEDRON, 2001, 57 (22) :4719-4728

[4] High-throughput screening identifies inhibitors of the SARS coronavirus main proteinase [J].

Blanchard, JE ;

Elowe, NH ;

Huitema, C ;

Fortin, PD ;

Cechetto, JD ;

Eltis, LD ;

Brown, ED .

CHEMISTRY & BIOLOGY, 2004, 11 (10) :1445-1453

[5] Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides [J].

Bossharth, E ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2003, 5 (14) :2441-2444

[6] Synthesis of furo [2,3-b] pyridin-4(7H)-ones and related quinolinone via Bronsted acid-promoted cyclisation of alkynes [J].

Bossharth, Emmanuel ;

Desbordes, Philippe ;

Monteiro, Nuno ;

Balme, Genevieve .

TETRAHEDRON LETTERS, 2009, 50 (06) :614-616

[7] Novel nucleotide triphosphates as potent P2Y2 agonists [J].

Brookings, Daniel ;

Davenport, Richard J. ;

Davis, Jeremy ;

Galvin, Frances C. A. ;

Lloyd, Steve ;

Mack, Stephen R. ;

Owens, Ray ;

Sabin, Verity ;

Wynn, Joanne .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) :562-565

[8] Angular methoxy-substituted furo- and pyranoquinolinones as blockers of the voltage-gated potassium channel Kv1.3 [J].

Butenschön, I ;

Möller, K ;

Hänsel, W .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (08) :1249-1256

[9]

CARVALHO CF, 1984, CHEM COMMUN, P227

[10]

Chang GJ, 2000, DRUG DEVELOP RES, V50, P170, DOI 10.1002/1098-2299(200006)50:2<170::AID-DDR7>3.0.CO

← 1 2 →