Abstract
A novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid was prepared and identified. It was used as a recyclable catalyst for the synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2-c]chromenes with excellent yields through a one-pot three-component reaction of aromatic aldehydes, malononitrile, and activated phenols in aqueous media. This environmentally benign protocol was found to be fairly efficient and offer wide substrate flexibility. The basic ionic liquid could be reused several times without any obvious loss of catalytic activity.
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Posner GH (1986) Chem Rev 86:831
Trost BM (1995) Angew Chem Int Ed Engl 24:259
Touré BB, Hall DG (2009) Chem Rev 109:4439
Wessjohann LA, Rivera DG, Vercillo OE (2009) Chem Rev 109:796
Kobayahi S, Manabe K (2002) Acc Chem Res 35:209
Akiya N, Savage PE (2002) Chem Rev 102:2725
Li CJ (2005) Chem Rev 105:3095
Blackmond DG, Armstrong A, Coomber V, Wells A (2007) Angew Chem Int Ed 46:3798
Minakata S, Komatsu M (2009) Chem Rev 109:711
Ellis GP (1977) The chemistry of heterocyclic compounds: chromenes, chromanes, and chromones. Wiley, New York
Galil A, Riad FM, Sherif BY, Elnagdi SM (1982) Chem Lett 11:1123
Hafez EA, Elnagdi MH, Elagamey AG, Taweel FM (1987) Heterocycles 26:903
Sofan MA, Taweel FM, Elnagdi MH (1989) Liebigs Ann Chem 95:935
Andreani LL, Lapi E (1960) Bull Chim Farm 99:583
Foye WO (1991) Principi di chemico farmaceutica. Piccin, Padova, p 416
Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517
Khurana JM, Kumar S (2009) Tetrahedron Lett 50:4125
Jin TS, Zhang JS, Liu LB, Wang AQ, Li TS (2006) Synth Commun 36:2009
Balalaie S, Ramezanpour S, Bararjanian M, Gross JH (2008) Synth Commun 38:1078
Khurana JM, Nand B, Saluja P (2010) Tetrahedron 66:5637
Abdolmohammadi S, Balalaie S (2007) Tetrahedron Lett 48:3299
Khan AT, Lal M, Ali S, Khan MM (2011) Tetrahedron Lett 52:5327
Mehrabi H, Mireki MK (2011) Chin Chem Lett 22:1419
Tabatabaeian K, Heidari H, Mamaghani M, Mahmoodi NO (2012) Appl Organomet Chem 26:56
Khoobi M, Ma’mani L, Rezazadeh F, Zareie Z, Foroumadi A, Ramazani A, Shafiee A (2012) J Mol Catal A Chem 359:74
Mehrabi H, Abusaidi H (2010) J Iran Chem Soc 7:890
Heravi MM, Jani BA, Derikvand F, Bamoharram FF, Oskooie HA (2008) Catal Commun 10:272
Heravi MM, Sadjadi S, Haj NM, Oskooie HA, Bamoharram FF (2009) Catal Commun 10:1643
Seifi M, Sheibani H (2008) Catal Lett 126:275
Kidwai M, Saxena S (2006) Synth Commun 36:2737
Pasha MA, Jayashankara VP (2007) Indian J Chem Sect B 46:1328
Patra A, Mahapatra T (2008) J Chem Res 7:405
Surpur MP, Kshirsagar S, Samant SD (2009) Tetrahedron Lett 50:719
Mekheimer RA, Sadek KU (2009) J Heterocycl Chem 46:149
Mekheimer RA, Sadek KU (2009) Chin Chem Lett 20:271
Mobinikhaledi A, Moghanian H, Sasani F (2011) Synth React Inorg Met Org Chem 41:262
Jin TS, Xiao JC, Wang SJ, Li TS (2004) Ultrason Sonochem 11:393
Jin TS, Xie H, Xue YP, Li TS (2008) Asian J Chem 20:5145
Zhou D, Ren ZJ, Cao WG, Chen J, Deng HM (2008) J Heterocycl Chem 45:1865
Welton T (1999) Chem Rev 99:2071
Dupont J, Souza RF, Suarez PAZ (2002) Chem Rev 102:3667
Bourbigou HO, Magna L, Morvan D (2010) Appl Catal A Gen 373:1
Hallett JP, Welton T (2011) Chem Rev 111:3508
Yue CB, Fang D, Liu L, Yi TF (2011) J Mol Liq 163:99
Lee S (2006) Chem Commun 10:1049
Pucheault M, Vaultier M (2009) Top Curr Chem 290:83
Giernoth R (2010) Angew Chem Int Ed 49:2834
Sawant AD, Raut DG, Darvatkar NB, Salunkhe MM (2011) Green Chem Lett Rev 4:41
Shaabani A, Samadi S, Badri Z, Rahmati A (2005) Catal Lett 104:39
Gong K, Wang HL, Fang D, Liu ZL (2008) Catal Commun 9:650
Gong K, Wang HL, Fang D, Liu ZL (2009) J Heterocycl Chem 46:1145
Chen L, Huang XJ, Li YQ, Zhou MY, Zheng WJ (2009) Monatsh Chem 140:45
Shaterian HR, Oveisi AR (2011) J Iran Chem Soc 8:545
Zheng J, Li YQ (2011) Mendeleev Commun 21:280
Shaterian HR, Arman M, Rigi F (2011) J Mol Liq 158:145
Zhi HZ, Lv CX, Zhang Q, Luo J (2009) Chem Commun 10:2878
Zhi HZ, Luo J, Feng GA, Lv CX (2009) Chin Chem Lett 20:379
Jamal MRN, Mashkouri S, Sharifi A (2010) Mol Divers 14:473
Davoodnia A, Nishaburi AT, Behmadi H, Hoseini NT, Attar P (2010) Asian J Chem 22:7978
Shaabani A, Samadi S, Rahmati A (2007) Synth Commun 37:491
Karimi AR, Eslami C (2011) Lett Org Chem 8:150
Aziz AS, Agrody AM, Bedair AH, Corkery TC, Ata A (2004) Heterocycles 63:1793
Shi DQ, Wu N, Zhuang QY (2008) J Chem Res 9:542
Luo J, Xin T, Wang Y (2013) New J Chem 37:269
Acknowledgments
This project was financially sponsored and supported by the National Natural Science Foundation of China (No. 21002050), the Doctoral Fund of the Ministry of Education of China for New Teachers (No. 200802881029), the Zijin Star Project and the Excellence Initiative Project of NUST.
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Wang, Y., Luo, J., Xing, T. et al. Synthesis of a novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid and its application in one-pot synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2-c]chromenes in aqueous media. Monatsh Chem 144, 1871–1876 (2013). https://doi.org/10.1007/s00706-013-1066-8
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DOI: https://doi.org/10.1007/s00706-013-1066-8