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Synthesis 2017; 49(07): 1641-1647
DOI: 10.1055/s-0036-1588357
DOI: 10.1055/s-0036-1588357
paper
A Simple and Green Tandem Knoevenagel–Phospha-Michael Reaction for One-Pot Synthesis of 2-Oxindol-3-ylphosphonates Catalyzed by a DABCO-Based Ionic Liquid
Authors
Weitere Informationen
Publikationsverlauf
Received: 23. September 2016
Accepted after revision: 01. November 2016
Publikationsdatum:
06. Dezember 2016 (online)
Abstract
A simple, clean, and efficient approach for the one-pot synthesis of 2-oxindol-3-ylphosphonates has been successfully developed. With 7 mol% loading of the 1,4-diazabicyclo[2.2.2]octane-based ionic liquid catalyst, 2-oxindol-3-ylphosphonates form in good to excellent yields within short times. This tandem reaction involves a phospha-Michael addition to the activated alkenes, which form in situ by Knoevenagel condensation. The corresponding products are easily separated and purified by simple crystallization. The catalyst can be recycled five times without significant activity loss. This approach is readily amenable to large-scale synthesis.
Keywords
phosphonates - oxindoles - ionic liquid - Knoevenagel condensation - phospha-Michael addition - tandem reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588357.
- Supporting Information (PDF)
-
References
- 1a Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 1b Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA. Acc. Chem. Res. 1996; 29: 123
- 1c Ugi I. Pure Appl. Chem. 2001; 73: 187
- 1d Toure BB, Hall DG. Chem. Rev. 2009; 109: 4439
- 1e Sunderhaus JD, Martin SF. Chem. Eur. J. 2009; 15: 1300
- 2a Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
- 2b Joucla L, Djakovitch L. Adv. Synth. Catal. 2009; 351: 673
- 2c Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
- 2d Bartoli G, Bencivenni G, Dalpozzo R. Chem. Soc. Rev. 2010; 39: 4449
- 2e Kamano Y, Zhang HP, Ichihara Y, Kizu H, Komiyama K, Pettit GR. Tetrahedron Lett. 1995; 36: 2783
- 3 Sundberg RJ. The Chemistry of Indoles. Academic; New York: 1996
- 4a Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
Reference Ris Wihthout Link
- 4b Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
- 6a Onouchi H, Miyagawa T, Furuko A, Maeda K, Yashima E. J. Am. Chem. Soc. 2005; 127: 2960
- 6b Queffelec C, Petit M, Janvier P, Knight DA, Bujoli B. Chem. Rev. 2012; 112: 3777
- 7a Chelucci G, Orru G, Pinna GA. Tetrahedron 2003; 59: 9471
- 7b Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
- 7c Guo Y, Fu H, Chen H, Li X. Catal. Commun. 2008; 9: 1842
- 7d Li Y, Lu L.-Q, Das S, Pisiewicz S, Junge K, Beller M. J. Am. Chem. Soc. 2012; 134: 18325
- 8a Peyman A, Budt KH, Paning JS, Stowasser B, Ruppert D. Tetrahedron Lett. 1992; 33: 4549
- 8b Alonso E, Solis A, Del Pozo C. Synlett 2000; 698
- 9 Kafarski P, Lejczak B. Phosphorus Sulfur Silicon Relat. Elem. 1991; 63: 193
- 10 Allerberger F, Klare IJ. J. Antimicrob. Chemother. 1999; 43: 211
- 11a Chung SK, Kang DH. Tetrahedron: Asymmetry 1996; 7: 21
- 11b Dang Q, Liu Y, Cashion DK, Kasibhatla SR, Jiang T, Taplin F, Jacintho JD, Li H, Sun Z, Fan Y, Dare J, Tian F, Li W, Gibson T, Lemus R, Van Poelje PD, Potter SC, Erion MD. J. Med. Chem. 2011; 54: 153
- 11c Chen X, Kopecky DJ, Mihalic J, Jeffries S, Min X, Heath J, Deignan J, Lai S, Fu Z, Guimaraes C, Shen S, Li S, Johnstone S, Thibault S, Xu H, Cardozo M, Shen W, Walker N, Kaysers F, Wang Z. J. Med. Chem. 2012; 55: 3837
- 12a Jiang Z, Zhang Y, Ye W, Tan CH. Tetrahedron Lett. 2007; 48: 51
- 12b Sobhani S, Parizi ZP. Tetrahedron 2011; 67: 3540
- 12c Sobhani S, Parizi ZP, Razavi N. Appl. Catal., A 2011; 409–410: 162
- 12d Hashem S, Sakineh E, Mohammad MD. Tetrahedron 2013; 69: 4708
- 12e Kulkarni MA, Pandurangi VR, Desai UV, Wadgaonkar PP. C. R. Chim. 2012; 15: 745
- 12f Gaikwad DS, Undale KA, Shaikh TS, Pore DM. C. R. Chim. 2011; 14: 865
- 12g Mohammadi R, Kassaee MZ. J. Mol. Catal. A: Chem. 2013; 380: 152
- 12h Sobhani S, Pakdin-Parizi Z. RSC Adv. 2014; 4: 13071
- 12i Kolla SR, Lee YR. Tetrahedron 2012; 68: 226
- 12j Dar BA, Pandey N, Singh S, Bamezai RK, Sharma M, Vishwakarma RA, Singh B. Tetrahedron Lett. 2014; 55: 623
- 12k Sobhani S, Jahanshahi R. Synth. Commun. 2013; 43: 3247
- 12l Sobhani S, Ghasemzadeh MS, Honarmand M. Catal. Lett. 2014; 144: 1515
- 12m Sobhani S, Parizi ZP, Rezazadeh S. J. Organomet. Chem. 2011; 696: 813
- 12n Sobhani S, Rezazadeh S. Synlett 2010; 1485
- 12o Sobhani S, Bazrafshan M, Delluei AA, Parizi ZP. Appl. Catal., A 2013; 454: 145
- 13a Shakibaei GI, Samadi S, Ghahremanzadeh R, Bazgir A. J. Comb. Chem. 2010; 12: 295
- 13b Imani Shakibaei G, Feiz A, Ghahremanzadeh R, Bazgir A. Chem. Pharm. Bull. 2010; 58: 896
- 13c Hosseini-Sarvari M, Tavakolian M. New J. Chem. 2012; 36: 1014
- 14a Jain N, Kumar A, Chauhan S, Chauhan SM. S. Tetrahedron 2005; 61: 1015
- 14b Park S, Kazlauskas J. Curr. Opin. Biotechnol. 2003; 14: 432
- 15a Luo SZ, Mi XL, Zhang L, Liu S, Xu H, Cheng JP. Angew. Chem. Int. Ed. 2006; 45: 3093
- 15b Ni B, Zhang QY, Headley AD. Green Chem. 2007; 9: 737
- 15c Ranu BC, Banerjee S. Org. Lett. 2005; 7: 3049
- 15d Xu J.-M, Qian C, Liu B.-K, Wu Q, Lin X.-F. Tetrahedron 2007; 63: 986
- 15e Xu J.-M, Wu Q, Zhang Q.-Y, Zhang F, Lin X.-F. Eur. J. Org. Chem. 2007; 1798
- 16a Zhou L, Wang L. Chem. Lett. 2007; 35: 628
- 16b Luo SZ, Mi XL, Zhang L, Liu S, Xu H, Cheng JP. Tetrahedron 2007; 63: 1923
- 16c Hu SQ, Jiang T, Zhang ZF, Zhu AL, Han BX, Song JL, Xie Y, Li WJ. Tetrahedron Lett. 2007; 48: 5613
- 17a Albert SC. Green Chem. 2010; 12: 949
- 17b Sayin S, Yilmaz M. RSC Adv. 2014; 4: 2219
- 17c Petrović VP, Simijonović D, Živanović MN, Košarić JV, Petrović ZD, Markovića S, Marković SD. RSC Adv. 2014; 4: 24635
- 18a Wasserscheid P, Sesing M, Korth W. Green Chem. 2002; 4: 134
- 18b Luo Y, Pan AX, Xing M, Chen M, Xie JM. Adv. Mater. Res. 2012; 443: 917
- 18c Tran PH, Duus F, Le TN. Tetrahedron Lett. 2012; 53: 222
- 19a Ying AG, Xu SL, Liu S, Ni YX, Yang JG, Wu CL. Ind. Eng. Chem. Res. 2014; 53: 547
- 19b Epishina MA, Ovchinnikov IV, Kulikov AS, Makhova NN, Tartakovsky VA. Mendeleev Commun. 2011; 21: 21
- 19c Li ZH, Zhou ZM, Hao XY, Zhang J, Dong X, Liu YQ, Sun WW, Cao D. Appl. Catal., A 2012; 425: 28
- 20 Xu D.-Z, Liu Y, Shi S, Wang Y. Tetrahedron: Asymmetry 2010; 21: 2530
- 21a Xu D.-Z, Liu Y, Shi S, Wang Y. Green Chem. 2010; 12: 514
- 21b Xu D.-Z, Shi S, Wang Y. RSC Adv. 2013; 3: 23075
- 22 Yu Y.-Q, Xu D.-Z. Synthesis 2015; 47: 1869
- 23 Tong J, Yang C, Xu D.-Z. Synthesis 2016; 48: 3559
- 25 Liu Z.-M, Li N.-K, Huang X.-F, Wu B, Li N, Kwok C.-Y, Wang Y, Wang X.-W. Tetrahedron 2014; 70: 2406