Novel 2-pyrone synthesis via Michael addition of mandelic acid enolate to trans-1,2-diaroylethenes

被引：9

作者：

Barroso, S ^{[1
]}

Blay, G ^{[1
]}

Fernández, I ^{[1
]}

Pedro, JR ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 46期

关键词：

dioxolanone; lactones; enones; hydroxyacids;

D O I：

10.1016/j.tetlet.2004.09.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Aroyl-6-aryl-3-phenyl-2-pyrones are prepared in a three-step procedure involving the Michael addition of a cis-2,5-disubstituted-1,3-dioxolan-4-one, derived from mandelic acid, to trans-1,2-diaroylethenes, cyclisation to a furan under acidic conditions and lactonisation. The 2-pyrones can be also obtained directly from the Michael products under prolonged or strong acidic treatment with little decrease in yield. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8583 / 8586

页数：4

共 51 条

[21] Sequential 1,2-addition-electrocyclic ring closures involving acyclic α,β-unsaturated iminiums:: A formal [3+3] cycloaddition strategy to unique pyranyl spirocycles [J].

Hsung, RP ;

Shen, HC ;

Douglas, CJ ;

Morgan, CD ;

Degen, SJ ;

Yao, LJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :690-691

[22] A NOVEL FRIEDEL-CRAFTS REACTION - SYNTHESIS OF 4-PHENYLNAPHTHALEN-1-OLS [J].

HUANG, JT ;

SU, TL ;

WATANABE, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4811-4815

[23] NEW SYNTHESIS OF 2-PYRONES [J].

IZUMI, T ;

KASAHARA, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (05) :1673-1674

[24] PALLADIUM-CATALYZED SYNTHESIS OF ISOCOUMARIN AND 1-ISOQUINOLINONE DERIVATIVES [J].

IZUMI, T ;

NISHIMOTO, Y ;

KOHEI, K ;

KASAHARA, A .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) :1419-1424

[25] PREPARATION AND DIELS-ALDER REACTIVITY OF BENZOTHIENO[2,3-C]-PYRAN-3-ONES, AND BENZOTHIENO[3,2-C]-PYRAN-3-ONES, BENZOTHIOPHENE-2,3-QUINODIMETHANE ANALOGS - SYNTHESIS OF DIBENZOTHIOPHENES [J].

JACKSON, PM ;

MOODY, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :681-687

[26]

Kepe V, 1998, HETEROCYCLES, V48, P671

[27] SYNTHESIS OF ISOCOUMARINS, DIHYDROISOCOUMARINS, AND ISOQUINOLONES VIA PI-ALLYLNICKEL HALIDE AND PI-OLEFIN-PALLADIUM COMPLEXES [J].

KORTE, DE ;

HEGEDUS, LS ;

WIRTH, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (08) :1329-1336

[28]

KVITA V, 1992, CHIMIA, V46, P457

[29] Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes [J].

Larock, RC ;

Doty, MJ ;

Han, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8770-8779

[30]

Lee YS, 2000, ARCH PHARM, V333, P319, DOI 10.1002/1521-4184(200010)333:10<319::AID-ARDP319>3.0.CO

← 1 2 3 4 5 6 →