Synthesis 2018; 50(17): 3460-3466
DOI: 10.1055/s-0037-1610070
paper
© Georg Thieme Verlag Stuttgart · New York

Radical Addition/Cyclization Cascade: An Efficient Approach to Nitro-Containing Quinoline-2,4(1H,3H)-diones

Tao Yang
a  Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: liym@kmust.edu.cn
,
Jia-Li Zhou
a  Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: liym@kmust.edu.cn
,
Junpeng Li
b  State Key Laboratory of Advanced Technologies for Comprehensive Utilization of Platinum Metals, Kunming Institute of Precious Metals, Kunming 650106, P. R. of China
,
Yuehai Shen
a  Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: liym@kmust.edu.cn
,
Chuanzhu Gao
a  Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: liym@kmust.edu.cn
,
Ya-Min Li*
a  Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. of China   Email: liym@kmust.edu.cn
› Author Affiliations
We acknowledge the financial support from the National Natural Science Foundation of China (No. 21662021), the Applied Basic Research Foundation of Yunnan Province (2016DC032), and the Analysis and Testing Foundation of Kunming University of Science and Technology (2016T20130138, 20150725).
Further Information

Publication History

Received: 28 March 2018

Accepted after revision: 28 April 2018

Publication Date:
18 June 2018 (online)

Abstract

A radical addition/cyclization cascade of o-cyanoarylacrylamides with magnesium nitrate hexahydrate is developed. This reaction exhibits good functional group tolerance and wide substrate scope, provides a highly efficient and practical access to nitro-containing quinoline-2,4(1H,3H)-diones.

Supporting Information

 
  • References

    • 1a Kitamura S. Hashizume K. Iida T. Miyashitsa E. Shirata K. Kase H. J. Antibiot. 1986; 39: 1160
    • 1b Seong CM. Park WK. Park CM. Kong JY. Park NS. Bioorg. Med. Chem. Lett. 2008; 18: 738
    • 1c McCormick JL. McKee TC. Cardellina JH. Boyd MR. J. Nat. Prod. 1996; 59: 469
    • 1d Ahmed N. Brahmbhatt KG. Sabde S. Mitra D. Singh IP. Bhutani KK. Bioorg. Med. Chem. 2010; 18: 2872
    • 1e Han S. Zhang F.-F. Qian H.-Y. Chen L.-L. Pu J.-B. Xie X. Chen J.-Z. J. Med. Chem. 2015; 58: 5751
    • 1f Liu Y.-X. Zhao H.-P. Wang Z.-W. Li Y.-H. Song H.-B. Riches H. Beattie D. Gu Y.-C. Wang Q.-M. Mol. Divers. 2013; 17: 701
    • 2a Chauncey MA. Grundon MF. Synthesis 1990; 1005
    • 2b Klásek A. Mrkvička V. Pevec A. Košmrlj J. J. Org. Chem. 2004; 69: 5646
    • 2c Jung EJ. Park BH. Lee YR. Green Chem. 2010; 12: 2003
    • 3a Hamama WS. El-Din A. Hassanien E. Zoorob HH. Synth. Commun. 2014; 44: 1833
    • 3b Kumabe R. Nishino H. Tetrahedron Lett. 2004; 45: 703
    • 3c Kafka S. Proisl K. Kasparkova V. Urankar D. Kimmel R. Kosmrlj J. Tetrahedron 2013; 69: 10826
    • 3d Zografos AL. Mitsos CA. Igglessi-Markopoulou O. Org. Lett. 1999; 1: 1953
    • 3e Antolak SA. Yao Z.-K. Richoux GM. Slebodnick C. Carlier PR. Org. Lett. 2014; 16: 5204
    • 5a Shechter H. Conrad F. Daulton AL. Kaplan RB. J. Am. Chem. Soc. 1952; 74: 3052
    • 5b Jovel I. Prateeptongkum S. Jackstell R. Vogl N. Weckbecker C. Beller M. Adv. Synth. Catal. 2008; 350: 2493
    • 5c Olah GA. Ramaiah P. Rao CB. Graham S. Golam R. Trivedi NJ. Olah JA. J. Am. Chem. Soc. 1993; 115: 7246
    • 5d Kornbblum N. Powers JW. J. Org. Chem. 1957; 22: 455
    • 5e Emmons WD. J. Am. Chem. Soc. 1957; 79: 5528
    • 5f Suzuki H. Nonoyama N. Chem. Commun. 1996; 1783
    • 5g Deng G.-B. Zhang J.-L. Liu Y.-L. Liu B. Yang X.-H. Li J.-H. Chem. Commun. 2015; 51: 1886
    • 5h Zhou Y. Tang Z. Song Q. Chem. Commun. 2017; 53: 8972
    • 6a Maity S. Manna S. Rana S. Naveen T. Mallick A. Maiti D. J. Am. Chem. Soc. 2013; 135: 3355
    • 6b Li Y.-M. Wei X.-H. Li X.-A. Yang S.-D. Chem. Commun. 2013; 49: 11701
    • 6c Xue C. Fu C.-L. Ma S.-M. Chem. Commun. 2014; 50: 15333
    • 6d Shen T. Yuan Y.-Z. Jiao N. Chem. Commun. 2014; 50: 554
    • 6e Liu Y. Zhang J.-L. Song R.-J. Qian P.-C. Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 9017
    • 6f Yan H. Rong G. Liu D. Zheng Y. Chen J. Mao J. Org. Lett. 2014; 16: 6306
    • 6g Hao X.-H. Gao P. Song X.-R. Qiu Y.-F. Jin D.-P. Liu X.-Y. Liang Y.-M. Chem. Commun. 2015; 51: 6839
    • 6h Li X. Zhuang S. Fang X. Liu P. Sun P. Org. Biomol. Chem. 2017; 15: 1821
    • 7a Clegg W. Davies RP. Dunbar L. Feeder N. Liddle ST. Mulvey RE. Snaith R. Wheatley AE. H. Chem. Commun. 1999; 1401
    • 7b Malamas MS. Erdei J. Gunawan I. Barnes K. Johnson M. Hui Y. Turner J. Hu Y. Wagner E. Fan K. Olland A. Bard J. Robichaud AJ. J. Med. Chem. 2009; 52: 6314
    • 7c Jie S. Zhang S. Sun W.-H. Eur. J. Inorg. Chem. 2007; 5584
    • 8a Zhou C. Larock RC. J. Am. Chem. Soc. 2004; 126: 2302
    • 8b Zhao B. Lu X. Org. Lett. 2006; 8: 5987
    • 8c Miura T. Nakazawa H. Murakami M. Chem. Commun. 2005; 2855
    • 8d Lindh J. Sjoberg PJ. R. Larhed M. Angew. Chem. Int. Ed. 2010; 49: 7733
    • 8e Ma Y. You J. Song F. Chem.–Eur. J. 2013; 19: 1189
    • 8f Tsui GC. Glenadel Q. Lau C. Lautens M. Org. Lett. 2011; 13: 208
    • 8g Xia G. Han X. Lu X. Org. Lett. 2014; 16: 2058
    • 9a Curran DP. In Comprehensive Organic Synthesis . Vol. IV Trost BM. Flemming I. Pergamon Press; Oxford: 1991
    • 9b Kim S. Adv. Synth. Catal. 2004; 346: 19
    • 9c Beckwith AL. J. Raner KD. J. Org. Chem. 1992; 57: 4954
    • 10a Forrester AR. Gill M. Thomson RH. J. Chem. Soc., Perkin Trans. 1 1974; 621
    • 10b Kraus GA. Sy JO. J. Org. Chem. 1989; 54: 77
    • 10c Snider BB. Buckman BO. J. Org. Chem. 1992; 57: 322
    • 10d Montevecchi PC. Navacchia ML. Spagnolo P. J. Org. Chem. 1997; 62: 5846
    • 10e Streuff J. Feurer M. Bichovski P. Frey G. Gellrich U. Angew. Chem. Int. Ed. 2012; 51: 8661
    • 10f Zhao WX. Montgomery J. Angew. Chem. Int. Ed. 2015; 54: 12683
    • 11a Fu H. Wang S.-S. Li Y.-M. Adv. Synth. Catal. 2016; 358: 3616
    • 11b Wang S.-S. Fu H. Shen Y. Sun M. Li Y.-M. J. Org. Chem. 2016; 81: 2920
    • 11c Wang S.-S. Fu H. Wang G. Sun M. Li Y.-M. RSC Adv. 2016; 6: 52391
    • 11d Li Y.-M. Wang S.-S. Yu F.-C. Shen Y. Chang K.-J. Org. Biomol. Chem. 2015; 13: 5376
    • 11e Wang S. Huang X. Wang Q. Ge Z. Wang X. Li R. RSC Adv. 2016; 6: 11754
  • 12 Taniguchi T. Fujii T. Ishibashi H. J. Org. Chem. 2010; 75: 8126