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Synthesis 2015; 47(22): 3611-3617
DOI: 10.1055/s-0034-1378875
DOI: 10.1055/s-0034-1378875
paper
Enaminone-Based Three-Component Reactions for the Diastereoselective Synthesis of Fused Tetrahydropyridines
Further Information
Publication History
Received: 08 May 2015
Accepted after revision: 03 July 2015
Publication Date:
14 August 2015 (online)
Abstract
An environmentally benign multicomponent synthetic method has been realized for the diastereoselective construction of fused tetrahydropyridines. Structurally diverse products have been acquired with generally good yields via the assembly of simple starting materials, enaminones or nitroenamines, o-aminophenols, and cinnamaldehydes, in the presence of lactic acid in water–ethanol media.
Key words
enaminone - transamination - multicomponent reaction - polycyclic product - aqueous synthesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378875.
- Supporting Information
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References
-
1a Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 1b Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2009; 48: 3224
- 1c Harvey AL. Curr. Opin. Chem. Biol. 2007; 11: 480
- 1d Newman DJ, Cragg GM, Snader KM. J. Nat. Prod. 2003; 66: 1022
- 1e Breinbauer R, Vetter IR, Waldman H. Angew. Chem. Int. Ed. 2002; 41: 2879
- 1f Boldi AM. Curr. Opin. Chem. Biol. 2004; 8: 281
- 1g Toure BB, Hall DG. Chem. Rev. 2009; 109: 4439
- 2a Ulaczyk-Lesanko A, Hall DG. Curr. Opin. Chem. Biol. 2005; 9: 266
- 2b Nakata T. Chem. Rev. 2005; 105: 4314
- 2c Weinreb SM. Nat. Prod. Rep. 2007; 24: 931
- 2d Kotha S, Lahiri K. Synlett 2007; 2767
- 2e Sasaki M, Fuwa H. Synlett 2004; 1851
- 3a Liu Z, Zhang X, Larock RC. J. Am. Chem. Soc. 2005; 127: 15716
- 3b Dötz F, Brand JB, Ito S, Gherghel L, Müllen K. J. Am. Chem. Soc. 2000; 122: 7707
- 3c Kusama H, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2002; 124: 11592
- 3d Song G, Chen D, Pan C.-L, Crabtree RH, Li X. J. Org. Chem. 2010; 75: 74897
- 3e Sadaki M, Fuwa H, Ishikawa M, Tachibana K. Org. Lett. 1999; 1: 1075
- 3f Ji F, Li X, Wu W, Jiang H. J. Org. Chem. 2014; 79: 11246
-
3g Tahara Y.-k, Gake M, Matsubara R, Shibata T. Org. Lett. 2014; 16: 5980
- 3h Yokosaka T, Nemoto T, Nakayama H, Shiga N, Hamada Y. Chem. Commun. 2014; 50: 12775
- 3i Mondal SK, Manna SK, Mandal A, Samanta S, Ray JK. Tetrahedron Lett. 2014; 55: 6411
- 4a Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
-
4b Yu J, Feng S, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
- 4c de Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
- 4d Marson CM. Chem. Soc. Rev. 2012; 41: 7712
- 4e Brauch S, van Berkel SS, Westermann B. Chem. Soc. Rev. 2013; 42: 4948
- 4f Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2014; 43: 4633
- 4g Jiang B, Rajale T, Wever W, Tu S.-J, Li G. Chem. Asian J. 2010; 5: 2318
- 4h Gu Y. Green Chem. 2012; 14: 2091
- 4i Liu Y, Wang H, Wan J. Asian J. Org. Chem. 2013; 2: 374
- 5a Liéby-Muller F, Constantieux T, Rodriguez J. J. Am. Chem. Soc. 2005; 127: 17176
- 5b Dudognon Y, Du H, Roderiguez J, Bugaut X, Constantieux T. Chem. Commun. 2015; 51: 1980
- 5c Wang X, Wang S.-Y, Ji S.-J. Org. Lett. 2013; 15: 1954
- 5d Wan J.-P, Lin Y, Huang Q, Liu Y. J. Org. Chem. 2014; 79: 7232
- 5e Naqaraju A, Ramulu BJ, Shukla G, Srivastava A, Verma GK, Raqhuvanshi K, Singh MS. Green Chem. 2015; 17: 950
- 5f Chen Z, Wang B, Wang Z, Zhu G, Sun J. Angew. Chem. Int. Ed. 2013; 52: 2027
- 5g Sridharan V, Maiti S, Menéndez LC. Chem. Eur. J. 2009; 15: 4565
- 5h Enders D, Joie C, Deckers K. Chem. Eur. J. 2013; 19: 10818
- 5i Jiang B, Tu S.-J, Kaur P, Wever W, Li G. J. Am. Chem. Soc. 2009; 131: 11660
- 5j Ma Y.-L, Wang K.-M, Lin X.-R, Yan S.-J, Lin J. Tetrahedron 2014; 70: 6578
- 5k Su Y, Bouma MJ, Alcaraz L, Stocks M, Furber M. Chem. Eur. J. 2012; 18: 12624
- 6a Greenhill JV. Chem. Soc. Rev. 1977; 277
- 6b Stanovnik B, Svete J. Chem. Rev. 2004; 104: 2433
- 6c Elassara AA, El-Khairb AA. Tetrahedron 2003; 59: 8463
- 7a Jiang B, Li Q.-Y, Zhang H, Tu S.-J, Pindi S, Li G. Org. Lett. 2012; 14: 700
- 7b Hao W.-J, Wang J.-Q, Xu X.-P, Zhang S.-L, Wang S.-Y, Ji S.-J. J. Org. Chem. 2013; 78: 12362
- 7c Hao W.-J, Wang S.-Y, Ji S.-J. ACS Catal. 2013; 3: 2501
- 7d Debnath K, Singha K, Pramanik A. RSC Adv. 2015; 5: 31866
- 7e Cao C.-P, Lin W, Zhu M.-H, Huang Z.-B, Shi D.-Q. Chem. Commun. 2013; 49: 6983
- 8a Cao S, Jing Y, Liu Y, Wan J. Chin. J. Org. Chem. 2014; 34: 876
- 8b Wan J.-P, Pan Y.-J. Chem. Commun. 2009; 2768
- 8c Wan J.-P, Gan S.-F, Sun G.-L, Pan Y.-J. J. Org. Chem. 2009; 74: 2876
- 8d Zhou Y, Cao S, Wan J.-P. J. Org. Chem. 2014; 79: 9872
- 8e Muthusaravanan S, Sasikumar C, Devi Bala B, Perumal S. Green Chem. 2014; 16: 1297
- 8f Kantevary S, Addla D, Sridhar B. Synthesis 2010; 3745
- 8g Wan J.-P, Wang C, Pan Y. Tetrahedron 2011; 67: 922
- 8h Wan J.-P, Zhou R, Liu Y, Cai M. RSC Adv. 2013; 3: 2477
- 8i Cao S, Xin L, Liu Y, Wan J.-P, Wen C. RSC Adv. 2015; 5: 27373
- 8j Wan J.-P, Zhou Y, Jiang K, Ye H. Synthesis 2014; 46: 3256
- 9a Nakao A, Ohkawa N, Nagasaki T, Kagari T, Doi H, Shimozato T, Ushiyama S, Aoki K. Bioorg. Med. Chem. Lett. 2010; 20: 4774
- 9b Aeluri R, Alla M, Bommena VR, Murthy R, Jain N. Asian J. Org. Chem. 2012; 1: 71
- 9c Kálai T, Balog M, Szabó A, Gulyás G, Jekő J, Sümegi B, Hideg K. J. Med. Chem. 2009; 52: 1619
- 10a Yang J, Tan J.-N, Gu Y. Green Chem. 2012; 14: 3304
- 10b Wan J.-P, Lin Y, Hu K, Liu Y. RSC Adv. 2014; 4: 20499
- 10c Cao S, Zhong S, Hu C, Wan J.-P, Wen C. Chin. J. Chem. 2015; 33: 568
- 11 CCDC 1062710 (4a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 12 Liu Y, Zhou R, Wan J.-P. Synth. Commun. 2013; 43: 2475
- 13 El-Taweel FM. A. A, Elnagdi MH. J. Heterocycl. Chem. 2001; 38: 981
For reviews, see:
For selected recent reviews on MCRs, see:
For reviews on enaminone-based synthesis:
For selected recent references:
For a review, see:
For selected examples, see:
For references on biological function of tetrahydropyridines, see:
For the application of lactic acid in organic synthesis, see: