A Highly Diastereoselective Three-component Domino Reaction in Water Yielding Poly-substituted 4,5-Dihydropyrroles
Guangjing Tong
Jiangsu Provincial Xuzhou Pharmaceutical Vocational College, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorHaiwei Xu
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
Search for more papers by this authorWei Fan
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
Search for more papers by this authorCorresponding Author
Bo Jiang
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China, Tel.: 0086-0516-83500065; Fax: 0086-0516-83500065Search for more papers by this authorShuliang Wang
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
Search for more papers by this authorCorresponding Author
Shujiang Tu
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China, Tel.: 0086-0516-83500065; Fax: 0086-0516-83500065Search for more papers by this authorGuangjing Tong
Jiangsu Provincial Xuzhou Pharmaceutical Vocational College, Xuzhou, Jiangsu 221116, China
Search for more papers by this authorHaiwei Xu
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
Search for more papers by this authorWei Fan
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
Search for more papers by this authorCorresponding Author
Bo Jiang
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China, Tel.: 0086-0516-83500065; Fax: 0086-0516-83500065Search for more papers by this authorShuliang Wang
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
Search for more papers by this authorCorresponding Author
Shujiang Tu
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 211116, China, Tel.: 0086-0516-83500065; Fax: 0086-0516-83500065Search for more papers by this authorAbstract
An efficient methodology for highly diastereoselective synthesis of poly-substituted 4,5-dihydropyrrole derivatives from readily available common reactants in water has been developed. During domino processes, the formation of pyrrole skeleton and its C2-hydroxylation and C3-arylamination were readily achieved via metal-free [3+2] heterocyclization in a one-pot operation.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| cjoc_201300249_sm_suppl.pdf1 MB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1a Fattorusso, E.; Taglialatela-Scafati, O., Modern Alkaloids: Structure, Isolation, Synthesis and Biology, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008.
- 1b Castellano, S.; Fiji, H. D. G.; Kinderman, S. S.; Watanabe, M.; deLeon, P.; Tamanoi, F.; Kwon, O.. J. Am. Chem. Soc., 2007, 129, 5843.
- 1c Carmeli, S.; Moore, R. E.; Patterson, G. M. L.. Tetrahedron, 1991, 47, 2087.
- 1d Marti, C.; Carreira, E. M.. J. Am. Chem. Soc., 2005, 127, 11505.
- 2 Krishna, M. C.; DeGraff, W.; Hankovszky, O. H.; Sar, C. P.; Kalai, T.; Jeko, J.; Russo, A.; Mitchell, J. B.; Hideg, K.. J. Med. Chem., 1998, 41, 3477.
- 3 Anderson, W. K.; Milowsky, A. S.. J. Med. Chem., 1987, 30, 2144.
- 4 Sugden, J. K.; Tavakoli Saberi, M. R.. Eur. J. Med. Chem., 1979, 14, 189.
- 5 Lee, Y.; Ling, K.-Q.; Lu, X.; Silverman, R. B.; Shepard, E. M.; Dooley, D. M.; Sayre, L. M.. J. Am. Chem. Soc., 2002, 124, 12135.
- 6a Flogel, O.; Ghislaine, M.; Amombo, O.; Reissig, H.-U.; Zahn, G.; Brugam, I.; Hartl, H.. Chem. Eur. J., 2003, 9, 1405.
- 6b Amombo, M. O.; Hausherr, A.; Reissig, H.-U.. Synlett, 1999, 1871.
- 6c Sawadjoon, S.; Samec, J. S. M.. Org. Biomol. Chem., 2011, 9, 2548.
- 6d Ishikawa, S.; Noguchi, F.; Kamimura, A.. J. Org. Chem., 2010, 75, 3578.
- 6e Sun, W.; Ma, X.; Hong, L.; Wang, R.. J. Org. Chem., 2011, 76, 7826.
- 6f Ding, C.-H.; Dai, L.-X.; Hou, X.-L.. Tetrahedron, 2005, 61, 9586.
- 6g Katz, J. D.; Overman, L. E.. Tetrahedron, 2004, 60, 9559.
- 6h Christian, D.; Suzanne, G.. Synthesis, 1981, 466.
- 7 Zhang, Y.; Raines, A. J.; Flowers II, R. A.. J. Org. Chem., 2004, 69, 6267.
- 8a Zhu, Y.; Zhai, C.; Yue, Y.; Yang, L.; Hu, W.. Chem. Commun., 2009, 1362.
- 8b Zhang, X.; Ji, J.; Zhu, Y.; Jing, C.; Li, M.; Hu, W.. Org. Biomol. Chem., 2012, 10, 2133.
- 8c Ghorai, M. K.; Tiwari, D. P.. J. Org. Chem., 2013, 78, 2617.
- 8d Shi, F.; Luo, S.-W.; Tao, Z.-L.; He, L.; Yu, J.; Tu, S.-J.; Gong, L.-Z.. Org. Lett., 2011, 13, 4680.
- 9a
Tietze, L. F.;
Brasche, G.;
Gerike, K.,
Domino Reactions in Organic Chemistry, Wiley-VCH, Weinheim, 2006.
10.1002/9783527609925 Google Scholar
- 9b Padwa, A.. Chem. Soc. Rev., 2009, 38, 3072.
- 9c Tietze, L. F.; Kinzel, T.; Brazel, C. C.. Acc. Chem. Res., 2009, 42, 367.
- 10a Li, C. J.; Chen, L.. Chem. Soc. Rev., 2006, 35, 68.
- 10b Li, C. J.. Chem. Rev., 2005, 105, 3095.
- 11a Toure, B. B.; Hall, D. G.. Chem. Rev., 2009, 109, 4439.
- 11b Nicolaou, K. C.; Chen, J. S.. Chem. Soc. Rev., 2009, 38, 299.
- 12a Groenendaal, B.; Ruijter, E.; Orru, R. V. A.. Chem. Commun., 2008, 5474.
- 12b Ismabery, N.; Lavila, R.. Chem.-Eur. J., 2008, 14, 8444.
- 12c Sunderhaus, J. D.; Martin, S. F.. Chem.-Eur. J., 2009, 15, 1300.
- 12d Ganem, B.. Acc. Chem. Res., 2009, 42, 463.
- 13a Santra, S.; Andreana, P. R.. Angew. Chem., Int. Ed., 2011, 50, 9418.
- 13b DÖmling, A.; Wang, W.; Wang, K.. Chem. Rev., 2012, 112, 3083.
- 13c Fustero, S.; SÁnchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A.. Chem. Rev., 2011, 111, 6984.
- 13d
Li, G.;
Wei, H. X.;
Kim, S. H.;
Carducci, M. D..
Angew. Chem., Int. Ed.,
2001,
40,
4277.
10.1002/1521-3773(20011119)40:22<4277::AID-ANIE4277>3.0.CO;2-I CAS PubMed Web of Science® Google Scholar
- 13e Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G.. Chem.-Asian J., 2010, 5, 2318.
- 14a Jiang, B.; Li, C.; Shi, F.; Tu, S.-J.; Kaur, P.; Wever, W.; Li, G.. J. Org. Chem., 2010, 75, 2962.
- 14b Jiang, B.; Tu, S.-J.; Kaur, P.; Wever, W.; Li, G.. J. Am. Chem. Soc., 2009, 131, 11660.
- 14c Jiang, B.; Yi, M.-S.; Tu, M.-S.; Wang, S.-L.; Tu, S.-J.. Adv. Synth. Catal., 2012, 354, 2504.
- 14d Ma, N.; Jiang, B.; Zhang, G.; Tu, S.-J.; Wever, W.; Li, G.. Green Chem., 2010, 12, 1357.
- 14e Jiang, B.; Yi, M.-S.; Shi, F.; Tu, S.-J.; Pindi, S.; McDowell, P.; Li, G.. Chem. Commun., 2012, 808.
- 14f Jiang, B.; Feng, B.-M.; Wang, S.-L.; Tu, S.-J.; Li, G.. Chem.-Eur. J., 2012, 18, 9823.
- 14g Wang, S.; Cheng, C.; Gong, F.; Wu, F.; Jiang, B.; Zhou, J.; Tu, S.. Chin. J. Chem., 2011, 29, 2101.
- 14h Tu, S.; Wu, S.; Han, Z.; Hao, W.. Chin. J. Chem., 2009, 27, 1148.
- 15a Wu, X.; Larhed, M.. Org. Lett., 2005, 7, 3327.
- 15b Kappe, C. O.. Chem. Soc. Rev., 2008, 37, 1127.
- 15c Ju, Y.; Varma, R. S.. J. Org. Chem., 2006, 71, 135.
- 15d Dallinger, D.; Kappe, C. O.. Chem. Rev., 2007, 107, 2563.
- 15e Kabri, Y.; Gellis, A.; Vanelle, P.. Green Chem., 2009, 11, 201.
- 15f Shaughnessy, K. H.; Devasher, R. B.. Curr. Org. Chem., 2005, 9, 585.
- 16 The single-crystal growth was carried out in co-solvent of EtOH and DMF at room temperature. Crystal data for 4n:C25H21Br2ClN2O2, crystal dimension 0.23 mm×0.15 mm×0.10 mm, Triclinic, space group P-1, a=11.9309(11) Å, b=14.0473(13) Å, c=15.0113(15) Å, α=100.801(2)o, β=90.9050(10)o, γ=97.8560(10)o, V=2445.9(4) Å3, Mr576.71, Z=4, λ=0.71073 Å, μ(Mo Kα)=3.448 mm−1, F(000)=1152, R1=0.1442.
