Visible-Light Photoredox-Catalyzed Cascade Reaction for the 
Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Lingna Wang; Tiancong Ma; Mingming Qiao; Qiangxian Wu; Deqing Shi; Wenjing Xiao

doi:10.1055/s-0037-1610907

Synthesis, Table of Contents

Synthesis 2019; 51(02): 522-529
DOI: 10.1055/s-0037-1610907

paper

Visible-Light Photoredox-Catalyzed Cascade Reaction for the Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Authors

Lingna Wang
Tiancong Ma
Mingming Qiao
Qiangxian Wu
Deqing Shi*

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China Email: chshidq@mail.ccnu.edu.cn
Wenjing Xiao

Abstract

All articles of this category

Abstract

A visible-light photoredox-catalyzed oxidation/[3+2] cycloaddition/oxidative aromatization cascade reaction of [(3,4-dihydroisoquinolin-2(1H)-yl)methyl]phosphonates and activated olefins or alkynes for the efficient synthesis of potentially biological active pyrrolo[2,1-a]isoquinoline-substituted phosphonates was developed. This transformation features mild reaction conditions (i.e., visible light irradiation, room temperature), molecular oxygen (O₂) as a green oxidant, simple ‘one-pot’ operation.

Key words

visible light catalysis - [3+2] cycloaddition - pyrrolo[2,1-a]isoquinoline - phosphonate - cascade reaction

Full Text

References

References

1a Westheimer FH. Science (Washington, D. C.) 1987; 235: 1173
1b Demmer CS. Krogsgaard-Larsen N. Bunch L. Chem. Rev. 2011; 111: 7981
1c Corbridge DE. C. Phosphorus: Chemistry, Biochemistry and Technology . CRC Press; Boca Raton: 2013. 6th ed.
1d Kirumakki S. Huang J. Subbiah A. Yao J. Rowland A. Smith B. Mukherjee A. Samarajeewa S. Clearfield A. J. Mater. Chem. 2009; 19: 2593
1e Spampinato V. Tuccitto N. Quici S. Calabrese V. Marletta G. Torrisi A. Licciardello A. Langmuir 2010; 26: 8400

2a Seto H. Kuzuyama T. Nat. Prod. Rep. 1999; 16: 589
2b Yoshino K. Kohno T. Morita T. Tsukamoto G. J. Med. Chem. 1989; 32: 1528
2c Han L.-B. Ono Y. Xu Q. Shimada S. Bull. Chem. Soc. Jpn. 2010; 83: 1086
2d Tan S.-J. Lim J.-L. Low Y.-Y. Sim K.-S. Lim S.-H. Kam T.-S. J. Nat. Prod. 2014; 77: 2068

3a Kamer PC. J. Leeuwen PW. N. M. Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis. Wiley; Chichester: 2012
3b McManus HA. Guiry PJ. Chem. Rev. 2004; 104: 4151
3c Birkholz MN. Freixa Z. van Leeuwen PW. Chem. Soc. Rev. 2009; 38: 1099
3d Tang W.-J. Zhang X.-M. Chem. Rev. 2003; 103: 3029
3e Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
3f Shi W. Luo Y.-D. Luo X.-C. Chao L. Zhang H. Wang J. Lei A.-W. J. Am. Chem. Soc. 2008; 130: 14713

4a Prier CK. Rankic DA. MacMillan DW. Chem. Rev. 2013; 113: 5322
4b Romero NA. Nicewicz DA. Chem. Rev. 2016; 116: 10075
4c Chen J.-R. Hu X.-Q. Lu L.-Q. Xiao W.-J. Chem. Soc. Rev. 2016; 45: 2044
4d Shaw MH. Twilton J. MacMillan DW. C. J. Org. Chem. 2016; 81: 6898
4e Gentry EC. Knowles RR. Acc. Chem. Res. 2016; 49: 1546
4f Chen J.-R. Hu X.-Q. Lu L.-Q. Xiao W.-J. Acc. Chem. Res. 2016; 49: 1911
4g Xie J. Jin H.-M. Hashmi AS. K. Chem. Soc. Rev. 2017; 46: 5193
4h Xu P. Li W.-P. Xie J. Zhu C.-J. Acc. Chem. Res. 2018; 51: 484

5a Luo K. Yang W.-C. Wu L. Asian J. Org. Chem. 2017; 6: 350
5b Rueping M. Zhu S.-Q. Koenigs RM. Chem. Commun. 2011; 47: 8679
5c Hari DP. König B. Org. Lett. 2011; 13: 3852
5d Xue Q.-C. Xie J. Jin H.-M. Cheng Y.-X. Zhu C.-J. Org. Biomol. Chem. 2013; 11: 1606
5e Rueping M. Vila C. Bootwicha T. ACS Catal. 2013; 3: 1676
5f Yoo W.-J. Kobayashi S. Green Chem. 2014; 16: 2438
5g Franz JF. Kraus WB. Zeitler K. Chem. Commun. 2015; 51: 8280
5h Xuan J. Zeng T.-T. Chen J.-R. Lu L.-Q. Xiao W.-J. Chem. Eur. J. 2015; 21: 4962
5i Bu M.-J. Lu G.-P. Cai C. Catal. Sci. Technol. 2016; 6: 413
5j Luo K. Chen Y.-Z. Yang W.-C. Zhu J. Wu L. Org. Lett. 2016; 18: 452
5k He Y. Wu H.-M. Toste FD. Chem. Sci. 2015; 6: 1194
5l Shaikh RS. Düsel SJ. S. König B. ACS Catal. 2016; 6: 8410
5m Wang X.-Z. Meng Q.-Y. Zhong J.-J. Gao X.-W. Lei T. Zhao L.-M. Li Z.-J. Chen B. Tung C.-H. Wu L.-Z. Chem. Commun. 2015; 51: 11256
5n Shaikh RS. Ghosh I. König B. Chem. Eur. J. 2017; 23: 12120

6a Quint V. Morlet-Savary F. Lohier JF. Lalevee J. Gaumont AC. Lakhdar S. J. Am. Chem. Soc. 2016; 138: 7436
6b Li C.-X. Tu D.-S. Yao R. Yan H. Lu C.-S. Org. Lett. 2016; 18: 4928
6c Wang C.-H. Li Y.-D. Yang Y.-D. Org. Lett. 2018; 20: 2382

7a Bailly C. Curr. Med. Chem. Anti-Cancer Agents 2004; 4: 363
7b Fan H. Peng J. Hamann MT. Hu JF. Chem. Rev. 2008; 108: 264
7c Pla D. Albericio F. Alvarez M. Anti-Cancer Agents Med. Chem. 2008; 8: 746
7d Marco E. Laine W. Tardy C. Lansiaux A. Iwao M. Ishibashi F. Bailly C. Gago F. J. Med. Chem. 2005; 48: 3796
7e Reddy MV. R. Rao MR. Rhodes D. Hansen MS. T. Rubins K. Bushman FD. Venkateswarlu Y. Faulkner D. J. Med. Chem. 1999; 42: 1901
7f Reddy SM. Srinivasulu M. Satyanarayana N. Kondapi AK. Venkateswarlu Y. Tetrahedron 2005; 61: 9242
7g Quesada AR. Gravalos MD. G. Puentes JL. F. Br. J. Cancer 1996; 74: 677

8a Yu C. Zhang Y. Zhang S. Li H. Wang W. Chem. Commun. 2011; 47: 1036
8b Zou Y.-Q. Lu L.-Q. Fu L. Chang N.-J. Rong J. Chen J.-R. Xiao W.-J. Angew. Chem. Int. Ed. 2011; 50: 7171

9a Guo H.-M. Zhou Q.-Q. Jiang X. Shi D.-Q. Xiao W.-J. Adv. Synth. Catal. 2017; 359: 4141
9b Che J.-Y. Xu X.-Y. Tang Z.-L. Gu Y.-C. Shi D.-Q. Bioorg. Med. Chem. Lett. 2016; 26: 1310
9c Wang Z.-Q. Yu Z.-H. Wang Y. Shi D.-Q. Synthesis 2012; 44: 1559

10 See Supporting Information for details of condition optimization, the procedure for the sunlight-driven experiment and gram-scale reaction.
11 CCDC 1818810 (3a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
12 Fujiya A. Tanaka M. Yamaguchi E. Tada N. Itoh A. J. Org. Chem. 2016; 81: 7262

13a Condie AG. González-Gómez JC. Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464
13b Zhao G. Yang C. Guo L. Sun H. Chen C. Xia W. Chem. Commun. 2012; 48: 2337

14a Zakharov SV. Nuriazdanova GKh. Garifzyanov AR. Galkin VI. Cherkasov RA. Russ. J. Gen. Chem. 2004; 74: 873
14b Hu G.-B. Chen W.-Z. Ma D.-M. Zhang Y. Xu P.-X. Gao Y.-X. Zhao Y.-F. J. Org. Chem. 2016; 81: 1704

Supplementary Material

Supporting Information (PDF)