Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones
Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones
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DOI：
10.3390/30300088
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发表时间：
1998-03
期刊：
影响因子：
4.6
通讯作者：
D. Villemin;B. Martin;N. Bar
中科院分区：
文献类型：
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作者：
D. Villemin;B. Martin;N. Bar
UMR 6507，6 Boulevard du Marechal juin F-14050 Caen Cedex，Francetel(33)2 31 45 28 40，Fax(33)2 31 45 28 77，电子邮件：Didier.Villin@ismra.收件人：1998年2月19日/接受：1998年3月3日/发表：1998年3月5日摘要：3(2)-napthofuranone(1)在Al_2O_3-KF存在下与芳醛(4)缩合，得到芳基呋喃甲酮(5a-f)，无需聚焦。关键词：微波，有机合成，催化，催化干法反应、呋喃酮、月桂酮、介绍月桂酮(月桂酮、舒喘宁、马利西醇、来普西醇等)是与黄酮类化合物有关的植物天然黄色素[1]。极光的出现次数有限−第一个极光是在1943年才被发现的，由于合成方法有限，极光受到的关注非常有限。与类黄酮类化合物的类比表明，极光化合物可能具有有趣的生物学性质[2]。我们已经报道了具有羰基的五元环化合物，如四硝酸[3a]、吡唑酮[3b]、硫代水合花青素[3c]或吲哚酮[3d]，由于假平面结构，显示出高的碳酸性。因此，这些化合物在固体催化剂(氧化铝、粘土、Al_2O_3-KF)的存在下，很容易与醛缩合，而不需要溶剂(干缩)。在此，我们将该反应扩展到2-香豆酮(2)的同系物2-arylmethylene-3(2)-naphthofuranones.Naphthofuranone(1)的合成中，2-香豆酮(2)的同系物2-萘氧基乙酸(3)是一种有用的生长素激素。我们也有兴趣研究这类3(2)-萘基呋喃类化合物的生物学性质，这类化合物在较早的文献[5]中有描述，但迄今为止的研究很少。
Didier Villemin*, Benoit Martin and Nathalie BarEcole Nationale Superieure d'Ingenieurs de Caen (ISMRA) Universite de Caen,UMR 6507,6 Boulevard du Marechal Juin F-14050 Caen Cedex, FranceTel (33) 2 31 45 28 40, Fax (33) 2 31 45 28 77, E-mail: Didier.Villemin@ismra.frReceived: 19 February 1998 / Accepted: 3 March 1998 / Published: 5 March 1998Abstract: 3(2)-Naphthofuranone ( 1) was condensed in the presence of Al 2O3-KF with aromatic aldehydes(4) to give arylidenenaphthofuranones ( 5a-f ) without solvent under focused microwave irradiation.Keywords : Microwaves, organic synthesis, catalysis, dry reaction, furanone, aurone.IntroductionAurones (aurone, sulfuretol, maritimetol, leptosidol,etc.) are natural yellow pigments of plants related toflavonoids [1]. Aurones have a limited occurrence − thefirst aurone was discovered only in 1943 and, because ofthe limited methods of synthesis [1,3], aurones havereceived very limited attention. Analogy with flavonoidssuggests that aurones could have interesting biologicalproperties [2].We have already reported that five-membered ringcompounds with a carbonyl group, like tetronic acid [3a],pyrazolone [3b], thiohydanthoin [3c] or indanone [3d],exhibit a high carbon acidity due to the pseudo-planarstructure. These compounds consequently can becondensed easily with aldehydes in the presence of a solidcatalyst (alumina, clay, Al2O3-KF) without solvent (drycondensation).We report herein the extension of this reaction to thesynthesis of 2-arylmethylene-3(2)-naphthofuranones.Naphthofuranone (1), the homologue of 2-coumaranone(2), can be derived from 2-naphthoxyacetic acid (3), anuseful auxin hormone [4]. We are also interested instudying the biological properties of such 3(2)-naphthofuranones described in older literature [5] butpoorly studied to date.