在氧化亚锡催化下,吲哚、醛和丙二酸二甲酯在无溶剂条件下三组分反应合成了10种2-[(3-吲哚基)-甲基]丙二酸二甲酯衍生物.反应无溶剂污染,反应条件温和,收率为58％～74％.讨论了反应速度与取代基的关系,探讨了可能的缩合反应机理,并应用1H NMR、13C NMR、IR等技术手段确定了产品的结构.
参考文献
| [1] | Gribble GW..Recent developments in indole ring synthesis-methodology and applications [Review][J].Journal of the Chemical Society, Perkin Transactions 1,20000(0):1045-1075. |
| [2] | Francesco Epifano;Salvatore Genovese;Ornelio Rosati.Ytterbium triflate catalyzed synthesis of p-functionalized indole derivatives[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,20115(5):568-571. |
| [3] | Gerencser J;Panka G;Nagy T;Egyed O;Dorman G;Urge L;Darvas F.Procedure for the parallel preparation of 3-imidazo[1,2-alpha]pyridin-3-yl-propionic acid derivatives involving Meldrum's acid[J].Journal of combinatorial chemistry,20054(4):530-538. |
| [4] | Marcelo Vilches-Herrera;Ingo Knepper;Nayane de Souza.One-Pot, Three-Component Synthesis of 7-Azaindole Derivatives from N-Substituted 2-Amino-4-eyanopyrroles, Various Aldehydes, and Active Methylene Compounds[J].ACS combinatorial science,20127(7):434-441. |
| [5] | Nemes C.;Sapi J.;Laronze M.;Seghir H.;Auge F.;Laronze JY.;Jeannin L..A convenient synthesis of conformationally constrained beta-substituted tryptophans[J].Tetrahedron,200030(30):5479-5492. |
| [6] | Renzetti A;Dardennes E;Fontana A;De Maria P;Sapi J;Gerard S.TiCl4/Et3N-promoted three-component condensation between aromatic heterocycles, aldehydes, and active methylene compounds[J].The Journal of Organic Chemistry,200817(17):6824-6827. |
| [7] | Srivari Chandrasekhar;Vidyavathi Patro;Gangireddy Pavan Kumar Reddy.A ligaed-free copper(II)-￡atalyzecl three-component reaction in poly(ethylene glycol) medium: a versatile protocol for the preparation of selected 3-indole derivatives[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,201246(46):6223-6225. |
| [8] | Qu, Y.;Ke, F.;Zhou, L.;Li, Z.;Xiang, H.;Wu, D.;Zhou, X..Synthesis of 3-indole derivatives by copper sulfonato Salen catalyzed three-component reactions in water[J].Chemical communications,201113(13):3912-3914. |
| [9] | Fillion, E;Dumas, AM;Kuropatwa, BA;Malhotra, NR;Sitler, TC.Yb(OTf)(3)-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: One-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones[J].The Journal of Organic Chemistry,20061(1):409-412. |
| [10] | Aaron M.Dumas;Adam Seed;Alexander K.Zorzitto.A general and practical preparation of alkylidene Meldrum's acids[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,200740(40):7072-7074. |
| [11] | 郭圣荣;袁艳琴;张春牛.无溶剂无催化剂条件下二硫代氨基甲酸酯衍生物的合成研究[J].有机化学,2012(5):907-914. |
| [12] | Chunhua Lin;Zhaohui Xu;Weilin Liao.Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-l, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst[J].International journal of organic chemistry,20134(4):275-279. |
| [13] | 刘雄伟;潘博文;郭丰敏;曹煜;刘雄利;周英.双吲哚烷基类化合物在无催化剂和无溶剂条件下的高效合成[J].应用化学,2014(7):778-781. |
| [14] | 王方;赵耀明;汪朝阳.氧化亚锡催化直接熔融聚合法合成生物降解材料聚乳酸-聚乙二醇[J].材料导报,2005(2):118-120. |
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