期刊文献+

5-[(3-吲哚基)-甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物的高效合成 被引量:4

Efficient One-Pot Synthesis of 5-[(Indol-3-yl)-methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives
下载PDF
导出
摘要 在分子碘作用下,以吲哚、醛和2,2-二甲基-1,3-二噁烷-4,6-二酮为原料,通过三组分缩合反应合成了10种5-[(3-吲哚基)-甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮衍生物。当催化剂的用量为5%(摩尔分数)时,30℃反应60~90 min,收率为71.4%~97.3%。此外,还探讨了分子碘的催化机理。 Ten 5- [ (indol-3-yl) -methyl ] -2,2-dimethyl-1,3-dioxane-4,6-dione derivatives were synthesized by the three component condensation reaction of indole, aldehyde and 2,2-dimethyl-1,3-dioxane-4,6-dione using iodine as the catalyst. The results indicates that the yields range from 71.4% to 97. 3% at 30 ℃ for 60 - 90 rain using 5% molar fraction of iodine. Furthermore, a mechanism for the reaction catalyzed by iodine is proposed.
出处 《应用化学》 CAS CSCD 北大核心 2015年第3期278-283,共6页 Chinese Journal of Applied Chemistry
基金 国家科技攻关计划(2001BA323C) 江西省研究生创新基金(YC10A51)资助项目~~
关键词 二甲基二噁烷二酮 三组分反应 dimethyl-dioxane-dione iodine aldehydes three component condensation reaction
  • 相关文献

参考文献18

  • 1Wessjohann L A, Rivera D G, Vercillo O E. Multiple Multicomponent Macrocyclizations (MiBs) :A Strategic Development Toward Macrocycle Diversity [ J ]. Chem Rev, 2009,109 ( 2 ) : 796-814.
  • 2杨德利,李加荣,孙克宁,路红燕,刘明星,史大昕.TiCl_4催化一锅法三组分合成β-氨基酮化合物[J].有机化学,2013,33(11):2341-2348. 被引量:12
  • 3Francesco E. Salvatore G. Ornelio R. Ytterbium Triflate Catalyzed Synthesis of/3-Functionalized lndole Derivatives [ J ]. Tetrahedron Lett, 2011,52 ( 5 ) : 568 -571.
  • 4Janos G, Gabor P, Tamas N. Procedure for the Parallel Preparation of 3-Imidazo [ 1,2-a ] pyridin-3-yl-propionic Acid Derivatives Involving Meldrum's Acid[ J]. J Comb Chem,2005,7(5) :530-538.
  • 5Marcelo V H, Ingo K, Nayanede S. One-Pot, Three-Component Synthesis of 7-Azaindole Derivatives from N-Substituted 2- Amino-4-cyanopyrroles, Various Aldehydes, and Active Methylene Compounds[ J]. ACS Comb Sci,2012,14:434-441.
  • 6Janos G, Gyorgy D, Ferenc D. Meldrum s Acid in Muhicomponent Reactions:Applications to Combinatorial and Diversity- Oriented Synthesis [ J ]. QSAR Comb Sci, 2006,25 (5) : 439 -448.
  • 7Yuji O, Hitoshi H, Osamu Y. Meldrum's Acid in Organic Synthesis. 1. A Convenient One-Pot Syntheisis of Ethyl Indolepropionates [ J ]. Tetrahedron Lett, 1978,20 : 1759-1762.
  • 8Csaba N, Laurent J, Janos S. A Convenient Synthesis of Conformationally Constrained/3-Substitued Tryptophans [ J ]. Tetrahedron ,2000,56:5479-5492.
  • 9Andrea R, Emmanuel D, Antonella F. TiC14/Et3 N-Promoted Three-Component Condensation Between Aromatic Heterocycles, Aldehydes, and Active Methylene Compounds [ J ]. J Org Chem,2008,73 ( 17 ) : 6824-8427.
  • 10Srivari C,Vidyavathi P,Gangireddy P. A Ligand-free Copper( 1I )-catalyzed Three-component Reaction in Poly( ethylene glycol) Medium : A Versatile Protocol for the Preparation of Selected 3-Indole Derivatives [ J ]. Tetrahedron Lett,2012,53 : 6223 -6225.

二级参考文献50

  • 1张颖,徐冬梅,张可达.醋酸乙烯酯的可控/活性自由基聚合[J].功能高分子学报,2005,18(3):526-533. 被引量:7
  • 2李小青,杜晓华,徐振元.三氟甲磺酸盐催化甲苯硝化反应的研究[J].有机化学,2006,26(8):1111-1114. 被引量:21
  • 3许文静,张颖,张可达.衰减链转移自由基聚合醋酸乙烯酯[J].石油化工,2007,36(6):575-578. 被引量:2
  • 4Park E S, Yoon J S. Synthesis of Poly ( Vinyl Acetate )-Graft-Polystyrene and Application to Preparation of Porous Membranes[ J]. Appl Polym Sci,2001,82( 7 ) :1658-1667.
  • 5Hawker C J, Bosman A W, Harth E. New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerization [ J ]. Chem Rev, 2001,101 ( 12 ) : 3661-3688.
  • 6Matyjaszewski K, Xia J. Atom Transfer Radical Polymerization [ J ]. Chem Rev,2001,101 (9) :2921-2990.
  • 7Kwak Y, Goto A,Fukuda T,et al. Asystematic Study on Activation Processes in Organotellurium-Mediated Living Radical Polymerizations of Styrene, Methyl Methacrylate, Methyl Acrylate, and Vinyl Acetate [ J ]. Macromolecules,2006,39 ( 14 ) : 4671-4679.
  • 8Lacroix-Desmazes P, Severac R, Boutevin B. Reverse Iodine Transfer Polymerization of Methyl Acrylate and n-Butyl Anaylate [ J ]. Macromolecules,2005,38 ( 15 ) : 6299-6309.
  • 9Chiefari J, Chong Y K, Ercole F, et al. Living Free-Radical Polymerization by Reversible Addition-Fragmentation Chain Transfer: The RAF Process [ J ]. Macromolecules, 1998,31 ( 16 ) : 5559 -5562.
  • 10Iovu M C, Matyjaszewski K. Controlled/Living Radical Polymerization of Vinyl Acetate by Degenerative Transfer with Alkyl Iodides [ J ]. Macromolecules,2003,36 (22) :9346-9354.

共引文献53

同被引文献52

  • 1刘卉闵,张冬暖,果秀敏,李慧章.超声波辐射下β-吲哚衍生物的合成[J].合成化学,2004,12(5):505-507. 被引量:8
  • 2Wessjohann L A, Rivera D G, Vercillo O E. Muhiple Muhicomponent Macrocyclizations (MiBs) :A Strategic Develoment Toward Macrocycle Diversity[J]. Chem Rev,2009,109(2) :796-814.
  • 3Rovnyak G C, Kimball S D, Benyer B, et al. Calcium Entry Blocks and Activators: Conformational and Structural Deterninants of Dihydropyrinmidine Calcium Channel Modulators [ J ]. J Med Chem, 1995,38 ( 1 ) : 119-129.
  • 4Snider B B,Shi Z. Biomimetic Syntheses of Crambines A, B, C1, and C2 Revision of the Structures of Crambines B and C1 [J]. J Org Chem,1993,58(15) :3828-3839.
  • 5Arimoto H, Hayakawa I, Kuramoto M, et al. Absolute Stereochemistry of Halichtorine: A Potent Inhibitor of VCAM-1 Induction [ J ]. Tetrahedron Lett, 1998,39 ( 8 ) :861-862.
  • 6Makoto K,Chou T,Kaoru Y,et al. Halichlorine, an Inhibitor of VCAM-1 Induction from the Marine Sponge Halichondria Okadai Kadata[ J]. Tetrahedron Lett, 1996,37(22) :3867-3870.
  • 7Dipak P, Debajyoti B, Mukut G, et al. Green Chemsitry Approaches to the Rgioselective Synthesis of Spiro Heterobicyclic Rings Using Iodine as a New and Efficient Catalyst Under Solvent-free Conditions[ J]. Mol Divers ,2011,15:257-261.
  • 8Srinivasa R J, Diya V, Shubha J. NBS/AIBN Promoted One-Pot Multi Component Regioselective Synthesis of Spiro Heterobicyclic Rings via Biginlli-like Condensation Reaction [ J ]. J Chem Pharm Res,2012,4 ( 5 ) :2372 -2379.
  • 9Srinivasa R J, Diya V, Shubha J. Mcrowave-Assisted Synthesis of Spirofused Heterocycles Using Decatungstodivanadogermanic Heteropoly Acid as a Novel and Reusable Heterogeneous Catalyst under Solvent-Free Conditions[ J]. J Cata1,2013,2013 : 1-8.
  • 10Naser M, Khalil P, Masoud B, Soudabeh K. Synthesis of Spiro Heterobicyclic Rings Using Cellulose Sulfuric Acid Under Solvent-Free Conditions[ J]. Asian J Chem,2013,25(6) :3373-3375.

引证文献4

二级引证文献5

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部