One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones

Mingshu Wu; Jie Jiang; Zhongxiang Zhu; Qinghe Wang; Dulin Kong

doi:10.1055/s-0036-1590896

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(01): 139-145
DOI: 10.1055/s-0036-1590896

paper

One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones

Mingshu Wu*

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China eMail: wmsh@hainnu.edu.cn

,

Jie Jiang

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China eMail: wmsh@hainnu.edu.cn

,

Zhongxiang Zhu

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China eMail: wmsh@hainnu.edu.cn

,

Qinghe Wang

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China eMail: wmsh@hainnu.edu.cn

,

Dulin Kong

^bSchool of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A concise, atom-economic, and highly regio/stereoselective synthetic strategy was developed for the construction of phosphorus- and nitrogen-fused polycyclic skeleton derivatives. The one-pot, two-step, catalyst-free domino condensation/intramolecular cycloaddition reaction of various substituted 2-(vinylphosphoryloxy)benzaldehydes with pyrazolidin-3-one took place at room temperature. Three new bonds (C–C, 2 × C–N) and two new nitrogen and phosphorus heterocycles were simultaneously constructed. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

Key words

catalyst-free - stereoselectivity - nitrogen and phosphorus heterocycles - polycycles - intramolecular cycloaddition

Volltext

Referenzen

References

1a Pinheiro Ed. S. Antunes OA. C. Fortunak JM. D. Antiviral Res. 2008; 79: 143
1b Atherton FR. Hall MJ. Hassall CH. Holmes SW. Lambert RW. Lloyd WJ. Ringrose PS. Antimicrob. Agents Chemother. 1980; 18: 897
1c Atherton FR. Hassall CH. Lambert RW. J. Med. Chem. 1986; 29: 29
1d Cherenok S. Yushchenko O. Tanchuk V. Mischenko I. Samus N. Arkivoc 2012; (iv): 278
1e Albrecht L. Albrecht A. Krawczyk H. Jørgensen KA. Chem. Eur. J. 2010; 16: 28
1f Uludag H. Kousinioris N. Gao T. Kantoci D. Biotechnol. Prog. 2000; 16: 258

2a Chan T.-H. Xin Y.-C. von Itzstein M. J. Org. Chem. 1997; 62: 3500
2b Dayde B. Pierra C. Gosselin G. Surleraux D. Ilagouma AT. Laborde C. Volle J.-N. Virieux D. Pirat J.-L. Eur. J. Org. Chem. 2014; 1333
2c Ebetino FH. Soper DL. Dirr MJ. Lundy MW. Mieling G. Wos JA. deLong MA. Liu X. Phosphorus, Sulfur Silicon Relat. Elem. 2002; 177: 1725
2d Stoianova DS. Whitehead A. Hanson PR. J. Org. Chem. 2005; 70: 5880
2e Kim C.-E. Ryu T. Kim S. Lee K. Lee C.-H. Lee PH. Adv. Synth. Catal. 2013; 355: 2873
2f Maury C. Gharbaoui T. Royer J. Husson H.-P. J. Org. Chem. 1996; 61: 3687
2g Stoianova DS. Hanson PR. Org. Lett. 2001; 3: 3285

3a Kim C.-E. Son J.-Y. Shin S. Seo B. Lee PH. Org. Lett. 2015; 17: 908
3b Li X. Wang Y. Fu H. Jiang Y. Zhao Y. Bioorg. Chem. 2006; 34: 105
3c Li X. Zhang D. Pang H. Shen F. Fu H. Jiang Y. Zhao Y. Org. Lett. 2005; 7: 4919
3d Sadykova YM. Sadikova LM. Badrtdinova AR. Dobrynin AB. Burilov AR. Pudovik MA. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190: 2267
3e Petkova NI. Nikolova RD. Bojilova AG. Rodios NA. Kopf J. Tetrahedron 2009; 65: 1639

4 Bedalov A. Gatbonton T. Irvine WP. Gottschling DE. Simon JA. Proc. Natl. Acad. Sci. U. S. A. 2001; 98: 15113

5a Drabikova KP. T. Nosal R. Rackova L. Ambrozova G. Lojek AS. J. Harmatha J. Jancinova V. Neuroendocrinol. Lett. 2010; 31: 73
5b Hirao M. Posakony J. Nelson M. Hruby H. Jung M. Simon JA. Bedalov A. J. Biol. Chem. 2003; 278: 52773

6a Kosower E. Radkowsky A. Fairlamb A. Croft S. Neal R. Eur. J. Med. Chem. 1995; 30: 659
6b Boatman PD. Ogbu CO. Eguchi M. Kim H.-O. Nakanishi H. Cao B. Shea JP. Kahn M. J. Med. Chem. 1999; 42: 1367
6c Gardiner J. Abell AD. Tetrahedron Lett. 2003; 44: 4227
6d Liu B. Brandt JD. Moeller KD. Tetrahedron 2003; 59: 8515

7a Liang L. Huang Y. Org. Lett. 2016; 18: 2604
7b Yang Z.-W. Wang J.-F. Peng L.-J. You X.-L. Cui H.-L. Tetrahedron Lett. 2016; 57: 5219

8a Chen W. Yuan XH. Li R. Du W. Wu Y. Ding LS. Chen YC. Adv. Synth. Catal. 2006; 348: 1818
8b Chen W. Du W. Duan YZ. Wu Y. Yang SY. Chen YC. Angew. Chem. Int. Ed. 2007; 119: 7811
8c Mei G.-J. Zhu Z.-Q. Zhao J.-J. Bian C.-Y. Chen J. Chen R.-W. Shi F. Chem. Commun. 2017; 53: 2768
8d Wang X. Yang P. Zhang Y. Tang CZ. Tian F. Peng L. Wang LX. Org. Lett. 2017; 19: 646
8e Xin Y. Zhao J. Gu J. Zhu S. J. Fluorine Chem. 2011; 132: 402

9a Na R. Jing C. Xu Q. Jiang H. Wu X. Shi J. Zhong J. Wang M. Benitez D. Tkatchouk E. Goddard WA. Guo H. Kwon O. J. Am. Chem. Soc. 2011; 133: 13337
9b Na R. Liu H. Li Z. Wang B. Liu J. Wang M.-A. Wang M. Zhong J. Guo H. Tetrahedron 2012; 68: 2349

10a Shao C. Zhang Q. Cheng G. Cheng C. Wang X. Hu Y. Eur. J. Org. Chem. 2013; 6443
10b Shintani R. Fu GC. J. Am. Chem. Soc. 2003; 125: 10778
10c Shintani R. Hayashi T. J. Am. Chem. Soc. 2006; 128: 6330
10d Yoshimura K. Oishi T. Yamaguchi K. Mizuno N. Chem. Eur. J. 2011; 17: 3827

11 Fang X. Li J. Tao H.-Y. Wang C.-J. Org. Lett. 2013; 15: 5554
12 Liu W. Xu Y. Sun X. Lu D. Guo L. Synlett 2014; 25: 1093

13a Coldham I. Hufton R. Chem. Rev. 2005; 105: 2765
13b Hashimoto T. Maruoka K. Chem. Rev. 2015; 115: 5366
13c Padwa A. Angew. Chem., Int. Ed. Engl. 1976; 15: 123

14a Jiang J. Wu M. Zhu Z. Kong D. Synthesis 2017; 49: 3731
14b Li G. Wu M. Kong D. Liu R. Zhou X. Liu F. New J. Chem. 2014; 38: 3350
14c Li G. Wu M. Liu F. Jiang J. Synthesis 2015; 47: 3783

15a Du J. Xu X. Li Y. Pan L. Liu Q. Org. Lett. 2014; 16: 4004
15b Tong MC. Chen X. Tao HY. Wang CJ. Angew. Chem. Int. Ed. 2013; 52: 12377
15c Zhao H.-W. Li B. Pang H.-L. Tian T. Chen X.-Q. Song X.-Q. Meng W. Yang Z. Zhao Y.-D. Liu Y.-Y. Org. Lett. 2016; 18: 848
15d Najera C. Sansano JM. Curr. Org. Chem. 2003; 7: 1105
15e Sansano LM. Sibi MP. Chem. Rev. 2008; 108: 2887

16 CCDC 1549590 (5b) 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.
17 Furegati S. Binder M. Linden A. Rüedi P. Helv. Chim. Acta 2006; 89: 1351

Zusatzmaterial