Enaminone-Based Three-Component Reactions for the Diastereoselective Synthesis of Fused Tetrahydropyridines

Jie-Ping Wan; Shanshan Zhong; Yunyun Liu

doi:10.1055/s-0034-1378875

Synthesis, Table of Contents

Synthesis 2015; 47(22): 3611-3617
DOI: 10.1055/s-0034-1378875

paper

Enaminone-Based Three-Component Reactions for the Diastereoselective Synthesis of Fused Tetrahydropyridines

Jie-Ping Wan*

Key Laboratory of the Functional Small Organic Molecules, Ministry of Education, and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China Email: wanjieping@jxnu.edu.cn

,

Shanshan Zhong

Key Laboratory of the Functional Small Organic Molecules, Ministry of Education, and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China Email: wanjieping@jxnu.edu.cn

,

Yunyun Liu

Key Laboratory of the Functional Small Organic Molecules, Ministry of Education, and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China Email: wanjieping@jxnu.edu.cn

› Author Affiliations

Abstract

All articles of this category

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 synthesis

Full Text

References

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

For reviews, see:

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

For selected recent reviews on MCRs, see:

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

For reviews on enaminone-based synthesis:

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

For selected recent references:

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

For a review, see:

8a Cao S, Jing Y, Liu Y, Wan J. Chin. J. Org. Chem. 2014; 34: 876

For selected examples, see:

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

For references on biological function of tetrahydropyridines, see:

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

For the application of lactic acid in organic synthesis, see:

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

Supplementary Material

Supporting Information