4H-1-benzopyrans by a tandem SN2-SNAr reaction

被引：18

作者：

Bunce, Richard A. ^{[1
]}

Rogers, David ^{[1
]}

Nago, Takahiro ^{[1
]}

Bryant, Scott A. ^{[1
]}

机构：

[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 02期

关键词：

D O I：

10.1002/jhet.5570450238

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 2-fluoro-5-nitrobenzyl bromide with active methylene compounds in the presence of excess potassium carbonate in acetone leads to the formation of highly functionalized 4H-1-benzopyrans by a tandem S(N)2-SNAr reaction sequence. The reaction works well with beta-keto esters, beta-keto sulfones, beta-keto phosphine oxides, beta-keto phosphonates and beta-keto nitriles. The reaction is simple to perform and affords products in 50-92%

引用

页码：547 / 550

页数：4

共 10 条

[1]

ANDRIEUX J, 1982, B SOC CHIM FR II-CH, P309

[2] Benzo-fused heterocycles and carbocycles by intramolecular SNAr and tandem SN2-SNAr reactions [J].

Bunce, Richard A. ;

Nago, Takahiro ;

Sonobe, Nathan ;

Slaughter, LeGrande M. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (02) :551-557

[3] (±)-2-Alkyl-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a catalyst and pressure dependent tandem reduction-reductive amination reaction [J].

Bunce, Richard A. ;

Nago, Takahiro ;

Sonobe, Nathan .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) :1059-1064

[4] Structure-activity relationship studies of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA 14-1), an antagonist for antiapoptotic Bcl-2 proteins to overcome drug resistance in cancer [J].

Doshi, Jignesh M. ;

Tian, Defeng ;

Xing, Chengguo .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (26) :7731-7739

[5] O-arylation versus C-arylation: Copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls [J].

Fang, Yewen ;

Li, Chaozhong .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6427-6431

[6] PREPARATION OF SOLE POLYMETHINE ASTRAZON DYES [J].

GALE, DJ ;

WILSHIRE, JF .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1970, 23 (05) :1063-&

[7]

HERCOUET A, 1979, TETRAHEDRON LETT, P2995

[8] Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay.: 1.: Structure-activity relationships of the 4-aryl group [J].

Kemnitzer, W ;

Drewe, J ;

Jiang, SC ;

Zhang, H ;

Wang, Y ;

Zhao, JH ;

Jia, SJ ;

Herich, J ;

Labreque, D ;

Storer, R ;

Meerovitch, K ;

Bouffard, D ;

Rej, R ;

Denis, R ;

Blais, C ;

Lamothe, S ;

Attardo, G ;

Gourdeau, H ;

Tseng, B ;

Kasibhatla, S ;

Cai, SX .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) :6299-6310

[9] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].

STILL, WC ;

KAHN, M ;

MITRA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925

[10]

Torr R. S., 1979, J CHEM SOC PAKISTAN, V1, P15

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