Synthesis 2012; 44(17): 2699-2706
DOI: 10.1055/s-0032-1316687
paper
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene Catalyzed One-Pot Synthesis of 2,3-Diarylquinoxalines

Yang Lin
b   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China, Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: Yiyuanpeng@yahoo.com
,
Xiaoli Lei
b   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China, Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: Yiyuanpeng@yahoo.com
,
Qin Yang
a   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Jiangjun Yuan
a   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Qiuping Ding*
b   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China, Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: Yiyuanpeng@yahoo.com
,
Jingshi Xu
a   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Yiyuan Peng*
a   Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
b   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China, Fax: +86(791)88120396   Email: yypeng@jxnu.edu.cn   Email: Yiyuanpeng@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 25 April 2012

Accepted after revision: 13 June 2012

Publication Date:
23 July 2012 (online)


Abstract

A one-pot efficient and facile protocol for the direct synthesis of quinoxaline derivatives via tandem N-heterocyclic carbene (NHC)-catalyzed umpolung of aldehydes/oxidation of the benzoins to benzils/condensation of benzils with benzene-1,2-diamines has been developed.

Supporting Information

 
  • References

    • 1a Kim YB, Kim YH, Park JY, Kim SK. Bioorg. Med. Chem. Lett. 2004; 14: 541
    • 1b He W, Meyers MR, Hanney B, Spada A, Blider G, Galzeinski H, Amin D, Needle S, Page K, Jayyosi Perrone H. Bioorg. Med. Chem. Lett. 2003; 13: 3097
    • 1c Sakata G, Makino K, Kuraswa Y. Heterocycles 1988; 27: 2481
    • 1d Seitz LE, Suling WJ, Reynolds RC. J. Med. Chem. 2002; 45: 5604
    • 2a Brown DJ. The Chemistry of Heterocyclic Compounds, Quinoxalines: Supplement II. Vol. 61. Wiley; New York: 2004
    • 2b Brock ED, Lewis DM, Yousaf TI, Harper HH. (The Procter and Gamble Company USA) WO9951688, 1999 ; Chem. Abstr. 1999, 131, 287743.
    • 2c Dailey S, Feast JW, Peace RJ, Sage IC, Till S, Wood EL. J. Mater. Chem. 2001; 11: 2238
    • 2d O’Breien D, Weaver MS, Lidzey DG, Bradley DD. C. Appl. Phys. Lett. 1996; 69: 881
    • 3a Porter AE. A In Comprehensive Heterocyclic Chemistry . Katritzky AR, Rees CW. Pergamon; Oxford, 1984; 157:
    • 3b Woo GH. C, Snyder JK, Wan ZK. Prog. Heterocycl. Chem. 2002; 14: 279
    • 3c Brown DJ. Quinoxalines: Supplement II, In The Chemistry of Heterocyclic Compounds . Taylor EE. C, Wipf P. Wiley; New Jersey: 2004
    • 4a Zhao Z, Wisnoski DD, Wolkenberg SE, Leister WH, Wang Y, Lindsley CW. Tetrahedron Lett. 2004; 45: 4873
    • 4b More SV, Sastry MN. V, Wang C, Yao C. Tetrahedron Lett. 2005; 46: 6345
    • 4c Cai J, Zou J, Pan X, Zhang W. Tetrahedron Lett. 2008; 49: 7386
    • 4d More SV, Sastry MN. V, Yao C. Green Chem. 2006; 8: 91
    • 4e Bhosale RS, Sarda SR, Ardhapure SS, Jadhav WN, Bhusare SR, Pawar RP. Tetrahedron Lett. 2005; 46: 7183
    • 5a Sithambaram S, Ding Y, Li W, Shen X, Gaenzler F, Suib SL. Green Chem. 2008; 10: 1029
    • 5b Raw SA, Wilfred CD, Taylor JK. Org. Biomol. Chem. 2004; 2: 788

      Some reviews:
    • 6a Nair V, Vellalath S, Babu BP. Chem. Soc. Rev. 2008; 37: 2691
    • 6b Marion N, Diez-Gonzalez S, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2988
    • 6c Niemeier DO, Henseler A. Chem. Rev. 2007; 107: 5606
    • 6d Christmann M. Angew. Chem. Int. Ed. 2005; 44: 2632
    • 6e Enders D, Balensiefer T. Acc. Chem. Res. 2004; 37: 534
    • 6f Nair V, Bindu S, Sreekumar V. Angew. Chem. Int. Ed. 2004; 43: 5130
    • 7a Mavis ME, Yolacan C, Aydogan F. Tetrahedron Lett. 2010; 51: 4509
    • 7b John MD, Williamson C. Tetrahedron Lett. 2005; 46: 7337
    • 7c Xu L, Gao Y, Yin J, Li L, Xia C. Tetrahedron Lett. 2005; 46: 5317
    • 7d Iwamoto K, Kimura H, Oike M, Sato M. Org. Biomol. Chem. 2011; 9: 5948
    • 7e Iwamoto K, Kimura H, Oike M, Sato M. Org. Biomol. Chem. 2008; 6: 912
    • 7f Dvorak CA, Rawal VH. Tetrahedron Lett. 1998; 39: 2925
    • 7g Knight RL, Leeper FJ. Tetrahedron Lett. 1997; 38: 3611
  • 8 Shimakawa Y, Morikawa T, Sakaguchi S. Tetrahedron Lett. 2010; 51: 1786
    • 9a Chiarotto I, Feroci M, Orsini M, Feeney MM. M, Inesi A. Adv. Synth. Catal. 2010; 352: 3287
    • 9b Iwamoto KI, Hamaya M, Hashimoto N, Kimura H, Suzuki Y, Sato M. Tetrahedron Lett. 2006; 47: 7175
  • 10 Thomas KR. J, Lin JT, Tao YT, Chuena CH. J. Mater. Chem. 2002; 12: 3516
  • 11 Campbell KN, Mckenna JF. J. Org. Chem. 1939; 4: 198
  • 12 Khodabakhsh N, Mohammad AZ, Ziba T, Zahra H. J. Chin. Chem. Soc. (Taipei, Taiwan) 2008;  6:  1373 ; Chem. Abstr. 2009, 151, 289107