Synthesis 2017; 49(08): 1879-1883
DOI: 10.1055/s-0036-1588380
paper
© Georg Thieme Verlag Stuttgart · New York

Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines via Iodine-Initiated Reaction of Methyl Aryl Ketones with Amines under Neat Heating

Hui Xu
School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China   Email: zhangze@ustc.edu.cn
,
Ji-Chao Zeng
School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China   Email: zhangze@ustc.edu.cn
,
Fang-Jian Wang
School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China   Email: zhangze@ustc.edu.cn
,
Ze Zhang*
School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China   Email: zhangze@ustc.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 06 October 2016

Accepted after revision: 29 November 2016

Publication Date:
15 December 2016 (online)


Abstract

A neat heating protocol has been developed for metal-free synthesis of various 2,4,6-trisubstituted pyridines via iodine-initiated (in situ generated HI-catalyzed) condensation of methyl aryl ketones with amines and the following cyclization-aerobic oxidation. Large-scale synthesis and mechanistic investigation were also performed.

Supporting Information

 
  • References

  • 1 Kröhnke F. Synthesis 1976; 1
  • 2 Fang AG, Mello JV, Finney NS. Tetrahedron 2004; 60: 11075
  • 3 Chelucci G, Thummel RP. Chem. Rev. 2002; 102: 3129
  • 4 Islam A, Sugihara H, Arakawa H. J. Photochem. Photobiol., A 2003; 158: 131
    • 5a Newkome GR, Wang PC, Moorefield N, Cho TJ, Mohapatra PP, Li S, Hwang SH, Lukoyanova O, Echegoyen L, Palagallo JA, Iancu V, Hla SW. Science 2006; 312: 1782
    • 5b Constable EC, Dunphy EL, Housecroft CE, Kylberg W, Neuberger M, Schaffner S, Schofield ER, Smith CB. Chem. Eur. J. 2006; 12: 4600
    • 5c Wang P, Moorefield CN, Newkome GR. Angew. Chem. Int. Ed. 2005; 44: 1679
  • 6 Lohmeijer BG. G, Schubert US. J. Polym. Sci., A: Polym. Chem. 2003; 41: 1413
  • 7 Katritzky AR, Abdel-Fattah AA. A, Tymoshenko DO, Essawy SA. Synthesis 1999; 2114

    • For some selected examples in recent years, see:
    • 8a Moosavi-Zare AR, Zolfigol MA, Rezanejad Z. Can. J. Chem. 2016; 94: 626
    • 8b Tabrizian E, Amoozadeh A, Rahmani S, Imanifar E, Azhari S, Malmir M. Chin. Chem. Lett. 2015; 26: 1278
    • 8c Zarnegar Z, Safari J, Borjian-borujeni M. Chem. Heterocycl. Compd. 2015; 50: 1683
    • 8d Maleki B. Org. Prep. Proced. Int. 2015; 47: 173
    • 8e Alinezhad H, Tajbakhsh M, Ghobadi N. Synth. Commun. 2015; 45: 1964
    • 8f Moosavi-Zare AR, Zolfigol MA, Farahmand S, Zare A, Pourali AR. Synlett 2014; 25: 193
  • 9 Mahernia S, Mahdavi M, Adib M. Synlett 2014; 25: 1299
  • 10 Adib M, Ayashi N, Mirzaei P. Synlett 2016; 27: 417
  • 11 Xiang J.-C, Wang M, Cheng Y, Wu A.-X. Org. Lett. 2016; 18: 24
  • 12 Zhang X, Wang Z.-Q, Xu K, Feng Y.-Q, Zhao W, Xu X.-F, Yan Y.-L, Yi W. Green Chem. 2016; 18: 2313
  • 13 Huang H.-W, Ji X.-C, Wu W.-Q, Huang L.-B, Jian H.-F. J. Org. Chem. 2013; 78: 3774
  • 14 Rohokale RS, Koenig B, Dhavale DD. J. Org. Chem. 2016; 81: 7121
  • 15 Xu H, Wang F.-J, Xin M, Zhang Z. Eur. J. Org. Chem. 2016; 925
  • 16 Amoros-Marin L, Carlin RB. J. Am. Chem. Soc. 1959; 81: 733