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Synlett 2014; 25(09): 1299-1301
DOI: 10.1055/s-0033-1341109
letter
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of 2,4,6-Triarylpyridines via Solvent-Free Reaction between Acetophenoneoximes and Aldehydes

Shabnam Mahernia
School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Fax: +98(21)66495291   eMail: madib@khayam.ut.ac.ir
,
Mohammad Mahdavi
School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Fax: +98(21)66495291   eMail: madib@khayam.ut.ac.ir
,
Mehdi Adib*
School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Fax: +98(21)66495291   eMail: madib@khayam.ut.ac.ir
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Publikationsverlauf

Received: 17. Februar 2014

Accepted after revision: 13. März 2014

Publikationsdatum:
30. April 2014 (online)

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Abstract

An efficient synthesis of 2,4,6-triarylpyridines is described. Heating a mixture of an acetophenoneoxime and an aldehyde under solvent-free conditions afforded Kröhnke pyridines in excellent yields. In this method acetophenoneoximes are directly used for the preparation of Kröhnke pyridines under metal-free conditions.

Key words

2,4,6-triarylpyridines - acetophenoneoximes - aldehydes - solvent-free synthesis - cyclizations - heterocycles
 

  • References and Notes

  • 1 Kim BY, Ahn JB, Lee HW, Kang SK, Lee JH, Shin JS, Ahn SK, Hong CI, Yoon SS. Eur. J. Med. Chem. 2004; 39: 433
    CrossrefSuche in Google Scholar
  • 2 Enyedy IJ, Sakamuri S, Zaman WA, Johnson KM, Wang S. Bioorg. Med. Chem. Lett. 2003; 13: 513
    CrossrefSuche in Google Scholar
  • 3 Pillai AD, Rathod PD, Franklin PX, Patel M, Nivsarkar M, Vasu KK, Padh H, Sudarsanam V. Biochem. Biophys. Res. Commun. 2003; 301: 183
    CrossrefSuche in Google Scholar
  • 4 Klimešová V, Svoboda M, Waisser K, Pour M, Kaustová J. Farmaco 1999; 54: 666
    CrossrefSuche in Google Scholar
  • 5 Balasubramanian M, Keay JG In Comprehensive Heterocyclic Chemistry II . Vol. 5. Katritzky AR, Rees CW, Scriven EV. F. Chapt. 6 Pergamon Press; London: 1996: 245-300 ; and references cited therein
    CrossrefSuche in Google Scholar
  • 6 McAteer CH, Balasubramanian M, Murugan R In Comprehensive Heterocyclic Chemistry III . Vol. 7. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Chapt. 6 Elsevier Science; Oxford: 2008: 309-334 ; and references cited therein
    CrossrefSuche in Google Scholar
  • 7 Kröhnke F. Synthesis 1976; 1
    Thieme Connect
  • 8 Fang AG, Mello JV, Finney NS. Tetrahedron 2004; 60: 11075
    CrossrefSuche in Google Scholar
  • 9 Chelucci G, Thummel RP. Chem. Rev. 2002; 102: 3129
    CrossrefPubMedSuche in Google Scholar
  • 10 Islam A, Sugihara H, Arakawa H. J. Photochem. Photobiol., A 2003; 158: 131
    CrossrefSuche in Google Scholar
  • 13 Schaefer P, Hamprecht G, Heistracher E, Klintz R, Koenig H, Harreus A, Goetz N, Walter H, Westphalen K.-O, Misslitz U. US 5733850, 1998 ; Chem. Abstr. 1996, 125, 167792w
  • 17 Ren ZH, Zhang ZY, Yang BQ, Wang YY, Guan ZH. Org. Lett. 2011; 13: 5394 ; and references cited therein
    Suche in Google Scholar
  • 19 Adib M, Tahermansouri H, Aali Koloogani S, Mohammadi B, Bijanzadeh HR. Tetrahedron Lett. 2006; 47: 5957
    Suche in Google Scholar
  • 20 General Procedure for the Preparation of 2,4,6-Triarylpyridines (3) A mixture of the appropriate acetophenoneoxime (2 mmol) and the appropriate aldehyde (1.2 mmol) was stirred within a sealed tube in a silicone oil bath at 200 °C for 3 h. Progress of the reaction followed by TLC monitoring. Then the reaction mixture cooled to r.t., and the residue was purified by column chromatography using n-hexane–EtOAc (4:1) as eluent. The solvent was removed, and the solid residue was recrystallized from absolute EtOH. 2,4,6-Triphenylpyridine (3a) Yield: 92%; colorless crystals; mp 136 °C. IR (KBr): 3061, 3033, 2923, 1598, 1549, 1595, 1445, 1399, 1237, 1027, 873, 757, 692 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 7.40–7.60 (m, 9 H, 9 × CH), 7.78 (d, J = 8.0 Hz, 2 H, 2 × CH), 7.92 (s, 2 H, 2 × CH), 8.23 (d, J = 8.0 Hz, 4 H, 4 × CH). 13C NMR (125.8 MHz, CDCl3): δ = 117.2, 127.2, 127.3 and 128.8 (4 × CH), 129.0 (C), 129.1 and 129.2 (2 × CH), 139.1 (C), 139.6 (CH), 150.2 and 157.5 (2 × C). MS (EI): m/z (%) = 307 (100) [M+], 289 (6), 276 (5), 230 (68), 207 (15), 202 (44), 179 (5), 165 (6), 151 (7), 127 (6), 102 (8), 77 (28), 51 (12).
    • 21a Lombard R, Stephan J.-P. Bull. Soc. Chim. Fr. 1958; 1458
    • 21b Huang XQ, Li HX, Wang JX, Jia XF. Chin. Chem. Lett. 2005; 16: 607
      Suche in Google Scholar
  • 22 Tu S, Jia R, Jiang B, Zhang J, Zhang Y, Yao C, Ji S. Tetrahedron 2007; 63: 381
    CrossrefSuche in Google Scholar
  • 23 Tu S, Li T, Shi F, Wang Q, Zhang J, Xu J, Zhu X, Zhang X, Zhu S, Shi D. Synthesis 2005; 3045
    Thieme Connect