[DMAP-PEG_(1000)-DIL][BF_4]催化合成4H-苯并吡喃-4-亚磷酸酯
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摘要
以水溶性高分子聚乙二醇(PEG)为原料,合成PEG接枝4-二甲氨基吡啶(DMAP)双阳离子功能化离子液体[DMAP-PEG_(1000)-DIL][BF_4]。采用~1HNMR、~(13)CNMR、FTIR、ESI-MS和TGA对其结构和热稳定性进行了表征。在[DMAP-PEG_(1000)-DIL][BF_4]用量为10%(以水杨醛的物质的量为基准,下同)、反应温度为100℃的条件下,不同取代基的水杨醛与丙二腈和亚磷酸三乙酯在水相中反应,制备了一系列4H-苯并吡喃-4-亚磷酸酯化合物,产率为83%～94%。该反应以水为溶剂,催化剂可重复使用5次,符合绿色化学的基本要求。
A novel poly(ethylene glycol)grafted 4-dimethylaminopyridine dicationic functionalized ionic liquid([DMAP-PEG_(1000)-DIL][BF_4])was synthesized with water-soluble polymer poly(ethylene glycol)as raw material.Its structure and thermal stability were characterized by ~1HNMR,~(13)CNMR,FTIR,ESI-MS and TGA.A series of 4H-chromen-4-yl-phosphonates in yields of 83%～94%were prepared by one-pot three-component reactions of different substituted salicylaldehyde with malononitrile and triethyl phosphite in water under the conditions of[DMAP-PEG_(1000)-DIL][BF_4]dosage being 10%different substituted salicylaldehyde and reaction temperature 100℃.This reaction used water as solvent and the catalyst could be reused for five times,which met the basic requirements of green chemistry.
A novel poly(ethylene glycol)grafted 4-dimethylaminopyridine dicationic functionalized ionic liquid([DMAP-PEG_(1000)-DIL][BF_4])was synthesized with water-soluble polymer poly(ethylene glycol)as raw material.Its structure and thermal stability were characterized by ~1HNMR,~(13)CNMR,FTIR,ESI-MS and TGA.A series of 4H-chromen-4-yl-phosphonates in yields of 83%～94%were prepared by one-pot three-component reactions of different substituted salicylaldehyde with malononitrile and triethyl phosphite in water under the conditions of[DMAP-PEG_(1000)-DIL][BF_4]dosage being 10%different substituted salicylaldehyde and reaction temperature 100℃.This reaction used water as solvent and the catalyst could be reused for five times,which met the basic requirements of green chemistry.
引文
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[19]Zhao Yadong(赵亚东),Gao Lei(郜蕾),Gao Jian(高健),et al.Synthesis of methyl oleate using a silica-immobilized SO3H-functionalized ionic liquid as an efficient catalyst[J].Fine Chemicals(精细化工),2018,35(1):81-86
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[22]Wang Y L,Luo J,Liu Z L.Synthesis of a novel 8-hydroxyquinoline functionalized poly(ethylene glycol)bridged dicationic ionic liquid and its application in palladium-catalyzed Heck reaction under solvent-free conditions[J].Journal of Organometallic Chemistry,2013,739:1-5.
[23]Wang Y L,Yue C,Li X,et al.Synthesis of a novel poly(ethylene glycol)grafted triethylamine functionalized dicationic ionic liquid and its application in one-pot synthesis of 2-amino-2-chromene derivatives in water[J].Comptes Rendus Chimie,2016,19(8):1021-1026.
[24]Wang Y L,Liu X G,Du C J,et al.Salicylaldoxime-functionalized poly(ethylene glycol)-grafted dicationic ionic liquid as a watersoluble and recyclable ligand for palladium-catalyzed Mizoroki-Heck reactions in aqueous phase[J].Synthetic Communications,2017,47(9):886-891.
[25]Dou Hui(窦辉),Gao Siyi(高思旖),Fu Zhaolong(付召龙),et al.Improved synthesis of substituted 2-amino-4H-chromene derivatives catalyzed by a new amino-functionalized basic ionic liquid1-(2-aminoethyl)-3-methylimidazolium imidazolide[J].Chinese Journal of Organic Chemistry(有机化学),2011,31(7):1056-1063.
[2]Jayashree P,Shanthi G,Perumal P T.Indium trichloride catalyzed one-pot synthesis of new(2-amino-3-cyano-4H-chromen-4-yl)phosphonic acid diethyl ester[J].Synlett,2009,6:917-920.
[3]Murthy S N,Madhav B,Reddy V P,et al.One-pot synthesis of2-amino-4H-chromen-4-yl phosphonate derivatives usingβ-cyclodextrin as reusable catalyst in water[J].Tetrahedron Letters,2010,51(28):3649-3653.
[4]Gaikwad D S,Undale K A,Shaikh T S,et al.An efficient multi-component synthesis of(2-amino-3-cyano-4H-chromen-4-yl)phosphonic acid diethyl ester[J].Comptes Rendus Chimie,2011,14(10):865-868.
[5]Das B,Balasubramanyam P,Reddy G C,et al.Simple,efficient,and catalyst-free synthesis of(2-amino-4H-1-benzopyran-4-yl)phosphonates in polyethylene glycol[J].Helvetica Chimica Acta,2011,94(7):1347-1350.
[6]Kulkarni M A,Pandurangi V R,Desai U V,et al.A practical and highly efficient protocol for multicomponent synthesis ofβ-phosphonomalononitriles and 2-amino-4H-chromen-4-yl phosphonates using diethylamine as a novel organocatalyst[J].Comptes Rendus Chimie,2012,15(9):745-752.
[7]Mohammadi R,Kassaee M Z.Sulfochitosan encapsulated nano-Fe3O4 as an efficient and reusable magnetic catalyst for green synthesis of 2-amino-4H-chromen-4-yl phosphonates[J].Journal of Molecular Catalysis A:Chemical,2013,380:152-158.
[8]Sobhani S,Honarmand M.Silica-bonded 2-hydroxyethylammonium acetate as an efficientand recyclable catalyst for the synthesis of2-amino-4H-chromen-4-yl phosphonates andβ-phosphonomalonates[J].Catalysis Letters,2013,143(5):476-485.
[9]Kalla R M N,Byeon S J,Heo M S,et al.Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine[J].Tetrahedron,2013,69(49):10544-10551.
[10]Dai P,Zha G F,Lai X Y,et al.Inorganic base catalyzed synthesis of(2-amino-3-cyano-4H-chromene-4-yl)phosphonate derivatives via multi-component reaction under mild and efficient conditions[J].RSC Advances,2014,4(108):63420-63424.
[11]Kolla S R,Lee Y R.Efficient one-pot synthesis ofβ-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives by ethylenediamine diacetate-catalyzed three-component reactions[J].Tetrahedron,2012,68(1):226-237.
[12]Darvish F,Abdollahzade A,Saravani D.Imidazole as an efficient catalyst for the synthesis of 2-amino-3-cyano-4H-chromen-4ylphosphonates[J].Research on Chemical Intermediates,2017,43(3):1487-1494.
[13]Kour P,Kumar A,Sharma R,et al.Synthesis of 2-amino-4H-chromen-4-ylphosphonates andβ-phosphonomalonates via tandem Knoevenagel-Phospha-Michael reaction and antimicrobial evaluation of newly synthesizedβ-phosphonomalonates[J].Research on Chemical Intermediates,2017,43(12),7319-7329.
[14]Krishnammagari S K,Cho B G,Jeong Y T.Choline chloride based eutectic solvent for the efficient synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives via multicomponent reaction under mild conditions[J].Phosphorus,Sulfur,and Silicon and the Related Elements,2018,193(5):306-316.
[15]Elinson M N,Nasybullin R F,Nikishin G I.Electrocatalytic fast and efficient multicomponent approach to medicinally relevant(2-amino-4H-chromen-4-yl)phosphonate Scaffold[J].Heteroatom Chemistry,2013,24(5):398-403.
[16]Mina J N,Reza K A.Designing bifunctional acid-base mesoporous organosilica nanocomposite and its application in green synthesis of4H-chromen-4-yl phosphonate derivatives under ultrasonic irradiation[J].Microporous and Mesoporous Materials,2016,223:10-17.
[17]Kour P,Kumar A,Rai V K.Aqueous microwave-assisted DMAPcatalyzed synthesis ofβ-phosphonomalonates and 2-amino-4H-chromen-4-ylphosphonates via a domino Knoevenagel-phosphaMichael reaction[J].Comptes Rendus Chimie,2017,20(2):140-145.
[18]Colacino E,Martinez J,Lamaty F,et al.PEG as an alternative reaction medium in metal-mediated transformations[J].Coordination Chemistry Reviews,2012,256(23/24):2893-2920.
[19]Zhao Yadong(赵亚东),Gao Lei(郜蕾),Gao Jian(高健),et al.Synthesis of methyl oleate using a silica-immobilized SO3H-functionalized ionic liquid as an efficient catalyst[J].Fine Chemicals(精细化工),2018,35(1):81-86
[20]Cecchini M M,Charnay C,Angelis F D,et al.Poly(ethylene glycol)-based ionic liquids:properties and uses as alternative solvents in organic synthesis and catalysis[J].Chemsuschem,2014,7(1):45-65.
[21]Xu Yisong(徐艺凇),Zhang Fengxiang(张凤香),Li Jiayun(厉嘉云),et al.Preparation and applications in organic reactions of polyethylene glycol functionalized ionic liquids[J].Progress in Chemistry(化学进展),2015,27(10):1400-1412.
[22]Wang Y L,Luo J,Liu Z L.Synthesis of a novel 8-hydroxyquinoline functionalized poly(ethylene glycol)bridged dicationic ionic liquid and its application in palladium-catalyzed Heck reaction under solvent-free conditions[J].Journal of Organometallic Chemistry,2013,739:1-5.
[23]Wang Y L,Yue C,Li X,et al.Synthesis of a novel poly(ethylene glycol)grafted triethylamine functionalized dicationic ionic liquid and its application in one-pot synthesis of 2-amino-2-chromene derivatives in water[J].Comptes Rendus Chimie,2016,19(8):1021-1026.
[24]Wang Y L,Liu X G,Du C J,et al.Salicylaldoxime-functionalized poly(ethylene glycol)-grafted dicationic ionic liquid as a watersoluble and recyclable ligand for palladium-catalyzed Mizoroki-Heck reactions in aqueous phase[J].Synthetic Communications,2017,47(9):886-891.
[25]Dou Hui(窦辉),Gao Siyi(高思旖),Fu Zhaolong(付召龙),et al.Improved synthesis of substituted 2-amino-4H-chromene derivatives catalyzed by a new amino-functionalized basic ionic liquid1-(2-aminoethyl)-3-methylimidazolium imidazolide[J].Chinese Journal of Organic Chemistry(有机化学),2011,31(7):1056-1063.