Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(10): 1533-1540
DOI: 10.1055/s-0035-1560411
DOI: 10.1055/s-0035-1560411
paper
Potassium-Exchanged Zirconium Hydrogen Phosphate [α-Zr(KPO4)2]-Catalyzed Synthesis of 2-Amino-4H-pyran Derivatives under Solvent-Free Conditions
Further Information
Publication History
Received: 16 December 2015
Accepted after revision: 20 January 2016
Publication Date:
25 February 2016 (online)
Abstract
A high-yielding, one-pot, three-component synthesis of functionalized 2-amino-4H-pyrans from β-dicarbonyl compounds, activated cyanomethylene compounds, and aldehydes, mediated by potassium-exchanged zirconium hydrogen phosphate [α-Zr(KPO4)2], is reported. The protocol shows excellent versatility, as it can be applied to aromatic, aliphatic, or α,β-unsaturated aldehydes under solvent-free conditions.
Key words
pyrans - amines - heterogeneous catalysis - solvent-free synthesis - multicomponent reactions - cyclizationsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560411.
- Supporting Information
-
References
- 1a Wickel SM, Citron CA, Dickschat JS. Eur. J. Org. Chem. 2013; 2906
- 1b Dong Z, Liu X, Feng J, Wang M, Lin L, Feng X. Eur. J. Org. Chem. 2011; 137
- 1c Henrikson JC, Ellis TK, King JB, Cichewicz RH. J. Nat. Prod. 2011; 74: 1959
- 1d Moafi L, Ahadi S, Bazgir A. Tetrahedron Lett. 2010; 51: 6270
- 1e Gibbons S, Denny BJ, Ali-Amine S, Mathew KT, Skelton BW, White AH, Gray AI. J. Nat. Prod. 2000; 63: 839
- 1f Uckun FM, Chen M, Vassilev AO, Huang H, Jan S.-T. Bioorg. Med. Chem. Lett. 2000; 10: 541
- 1g González R, Martín N, Seoane C, Marco JL, Albert A, Cano FH. Tetrahedron Lett. 1992; 33: 3809
- 1h Hatakeyama S, Ochi N, Numata H, Takano S. J. Chem. Soc., Chem. Commun. 1988; 1202
- 2a Litvinov YM, Shestopalov AM. Adv. Heterocycl. Chem. 2011; 103: 175
- 2b Kumar D, Reddy VB, Sharad S, Dube U, Kapur S. Eur. J. Med. Chem. 2009; 44: 3805
- 3 The Chemistry of Heterocyclic of Compounds . Vol. 31. Weissberger A, Taylor EC. Wiley; New York: 1977
- 4 Hafez EA. A, Elnagdi MH, Elagamey AG. A, El-Taweel FM. A. A. Heterocycles 1987; 26: 903
- 5 Nakhi A, Rahman MS, Archana S, Kishore R, Seerapu GP. K, Lalith KK, Haldar D, Pal M. Bioorg. Med. Chem. Lett. 2013; 23: 4195
- 6a Dekamin MG, Eslami M, Maleki A. Tetrahedron 2013; 69: 1074
- 6b Liu J, Li J, Zhang L, Song L, Zhang M, Cao W, Zhu S, Deng H, Shao M. Tetrahedron Lett. 2012; 53: 2469
- 6c Tian JJ, Guo HY. Youji Huaxue 2011; 31: 2009
- 6d Xu J.-C, Li W.-M, Zheng H, Lai Y.-F, Zhang P.-F. Tetrahedron 2011; 67: 9582
- 6e Bhattacharyya P, Pradhan K, Paul S, Das AR. Tetrahedron Lett. 2012; 53: 4687
- 6f Fotouhi L, Heravi MM, Fatehi A, Bakhtiari K. Tetrahedron Lett. 2007; 48: 5379
- 6g Peng Y, Song G. Catal. Commun. 2007; 8: 111
- 7 Kaupp G, Naimi-Jamal MR, Schmeyers J. Tetrahedron 2003; 59: 3753
- 8a Guo RY, An Z.-M, Mo L.-P, Wang R.-Z, Liu H.-X, Wang S.-X, Zhang Z.-H. ACS Comb. Sci. 2013; 15: 557
- 8b Maheshwar RB, Reddy GN, Reddy TV, Devi BL. A. P, Prasad RB. N, Yadav JS, Reddy BV. S. Tetrahedron Lett. 2013; 54: 2466
- 8c Karmakar B, Nayak A, Banerji J. Tetrahedron Lett. 2012; 53: 5004
- 8d Sun W.-B, Zhang P, Fan J, Chen S.-H, Zhang Z.-H. Synth. Commun. 2010; 40: 587
- 8e Surpur MP, Kshirsagar S, Samant S. Tetrahedron Lett. 2009; 50: 719
- 8f Devi I, Bhuyan PT. Tetrahedron Lett. 2004; 45: 8625
- 9 Safaei HR, Shekouhy M, Rahmanpur S, Shirinfeshan A. Green Chem. 2012; 14: 1696
- 11 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
- 12 Costantino U, Marmottini F, Curini M, Rosati O. Catal. Lett. 1993; 22: 333
- 13 Curini M, Rosati O, Costantino U. Curr. Org. Chem. 2004; 8: 591
- 14 Curini M, Epifano F, Chimichi S, Montanari F, Nocchetti M, Rosati O. Tetrahedron Lett. 2005; 46: 3497
- 15 Temperini A, Barattucci A, Bonaccorsi PM, Rosati O, Minuti L. J. Org. Chem. 2015; 80: 8102
- 16 Rajput JK, Kaur G. Catal. Sci. Technol. 2014; 4: 142
- 17 Suárez M, Salfrán E, Verdecia Y, Ochoa E, Alba L, Martín N, Martínez R, Quinteiro M, Seoane C, Novoa H, Blaton N, Peeters OM, De Ranter C. Tetrahedron 2002; 58: 953
- 18 Jin T.-S, Zhang J.-S, Xiao J.-C, Wang A.-Q, Li T.-S. Synlett 2004; 866
- 19 Abdel-Latif FF, Masahaly MM, El-Gawish EH. J. Chem. Res., Synop. 1995; 5: 178
- 20 Zhang G, Zhang Y, Yan J, Chen R, Wang S, Ma Y, Wang R. J. Org. Chem. 2012; 77: 878