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Synthesis 2010(24): 4228-4234
DOI: 10.1055/s-0030-1258274
DOI: 10.1055/s-0030-1258274
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSimple Selective Synthesis of 2,4- and 2,6-Diarylpyridines through Metal-Free Cyclocondensation of Aromatic Ketones with Ammonium Acetate
Further Information
Received
10 August 2010
Publication Date:
28 September 2010 (online)
Publication History
Publication Date:
28 September 2010 (online)

Abstract
A simple and selective one-pot synthesis of 2,4- and 2,6-diarylpyridines through the cyclocondensation reaction of aromatic ketones with ammonium acetate has been developed. The procedure is metal-free, convenient, and efficient, and the substrates are readily available.
Key words
diarylpyridines - selective - cyclocondensation - aromatic ketones - ammonium acetate
- 1a
Roth HJ.Kleemann A. Drug Synthesis in Pharmaceutical Chemistry Vol. 1: John Wiley and Sons; New York: 1988. - 1b
Michael JP. Nat. Prod. Rep. 2005, 22: 627 - 1c
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442 - 2a
Kawamura S.Hamada T.Sato R. J. Agric. Food Chem. 1991, 39: 2279 - 2b
Matolcsy G. Pesticide Chemistry Elsevier Scientific; Amsterdam: 1998. p.427-430 - 3a
Surry DS.Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 6338 - 3b
Cabeza JA.del Río I.Pérez-Carreňo E.Sánchez-Vega GM.Vázquez-García D. Angew. Chem. Int. Ed. 2009, 48: 555 - 4a
Togni A.Venanzi LM. Angew. Chem. Int. Ed. 1994, 33: 497 - 4b
Fache F.Schulz E.Tommasino ML.Lemaire M. Chem. Rev. 2000, 100: 2159 - 5a
Vaz AD.Coon MJ.Peegel H.Meenon KM. Drug Metab. Dispos. 1992, 20: 108 - 5b
Selvaraj M.Lee TG. Microporous Mesoporous Mater. 2005, 85: 52 - 6a
Bouras A.Boggetto N.Benatalah Z.de Rosny E.Sicsic S.Rebound-Ravaux M. J. Med. Chem. 1999, 42: 957 - 6b
Matrunola CA.Moody CJ.Robertson AAB.Warne MR. Tetrahedron Lett. 2003, 44: 1627 - 7a
Zhao LX.Sherchan J.Park JK.Jahng Y.Jeong BS.Jeong TC.Lee CS.Lee ES. Arch. Pharmacal. Res. 2006, 29: 1091 - 7b
Basnet A.Thapa P.Karki R.Na Y.Jahng Y.Jeong BS.Jeong TC.Lee CS.Lee ES. Bioorg. Med. Chem. 2007, 15: 4351 - 8a
Yamada S. Coord. Chem. Rev. 1999, 190: 537 - 8b
Kozhevnikov VN.Kozhevnikov DN.Nikitina TV.Rusinov VL.Chupakhin OL.Zabel M.Konig B. J. Org. Chem. 2003, 68: 2882 - 9
Lin C.Kagan CR. J. Am. Chem. Soc. 2003, 125: 336 - 10
Soto E.MacDonald JC.Cooper CGF.McGimpsey WG. J. Am. Chem. Soc. 2003, 125: 2838 - 11a
Sweetman BA.Müller-Bunz H.Guiry PJ. Tetrahedron Lett. 2005, 46: 4643 - 11b
Durola F.Sauvage JP.Wenger OS. Chem. Commun. 2006, 171 - 12 Recent review of de novo methods
for pyridine synthesis:
Henry GD. Tetrahedron 2004, 60: 6043 - For selected recent examples on the transition-metal-catalyzed synthesis of substituted pyridines:
- 13a
McCormick MM.Duong HA.Zuo G.Louie J. J. Am. Chem. Soc. 2005, 127: 5030 - 13b
Chang H.-T.Jeganmohan M.Cheng C.-H. Org. Lett. 2007, 9: 505 - 13c
Kase K.Goswami A.Ohtaki K.Tanabe E.Saino N.Okamoto S. Org. Lett. 2007, 9: 931 - 13d
Colby DA.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2008, 130: 3645 - 13e
Parthasarathy K.Jeganmohan M.Cheng C.-H. Org. Lett. 2008, 10: 325 - For selected recent examples on the synthesis of substituted pyridines via multicomponent reactions:
- 14a
Senaiar RS.Young DD.Deiter A. Chem. Commun. 2006, 1313 - 14b
Evdokimov N.Magedov IV.Kireev AS.Kornienko A. Org. Lett. 2006, 8: 899 - 14c
Dash J.Lechel T.Reissig H.-U. Org. Lett. 2007, 9: 5541 - 14d
Ranu BC.Jana R.Sowmiah S. J. Org. Chem. 2007, 72: 3152 - 14e
Zhu S.-L.Ji S.-J.Su X.-M.Sun C.Liu Y. Tetrahedron Lett. 2008, 49: 1777 - 14f
Sasada T.Sakai N.Konakahara T. J. Org. Chem. 2008, 73: 6905 - For selected recent examples on the synthesis of substituted pyridines via using ammonium acetate as the nitrogen source:
- 15a
Ladouceur GH.Cook JH.Doherty EM.Schoen WR.MacDougall ML.Livingston JN. Bioorg. Med. Chem. Lett. 2002, 12: 461 - 15b
Rodriguez H.Suarez M.Perez R.Petit A.Loupy A. Tetrahedron Lett. 2003, 44: 3709 - 15c
Bowman MD.Jacobson MM.Pujanauski BG.Blackwell HE. Tetrahedron 2006, 62: 4715 - 15d
Liéby-Muller F.Allais C.Constantieux T.Rodriguez J. Chem. Commun. 2008, 4207 - For selected recent examples on the synthesis of diarylpyridines via vapor-phase cyclization of acetophenone, formaldehyde and ammonia:
- 16a
Ratnamala A.Subrahmanyam M.Kumari VD. Appl. Catal., A 2004, 264: 219 - 16b
Selvaraj M.Lee TG. Microporous Mesoporous Mater. 2005, 85: 52 - For selected recent examples on the synthesis of diarylpyridines via arylation of the pyridine nucleus with organometallic reagents:
- 17a
Munoz B.Chixu C.McDonald IA. Biotechnol. Bioeng. 2000, 71: 78 - 17b
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 17c
Handy ST.Wilson T.Muth A. J. Org. Chem. 2007, 72: 8496 - For selected recent examples on the synthesis of diarylpyridines via palladium-catalyzed direct arylation of pyridine N-oxides:
- 18a
Campeau L.-C.Rousseaux S.Fagnou K. J. Am. Chem. Soc. 2005, 127: 18020 - 18b
Andersson H.Almqvist F.Olsson R. Org. Lett. 2007, 9: 1335 - 18c
Schipper DJ.El-Salfiti M.Whipp CJ.Fagnou K. Tetrahedron 2009, 65: 4977 - 19
Eliel EL.McBride RT.Kaufmann St. J. Am. Chem. Soc. 1953, 75: 4291 - 20a
Engler C.Heine H. Ber. Dtsch. Chem. Ges. 1873, 6: 638 - 20b
Reihm P. Justus Liebigs Ann. Chem. 1887, 238: 1 - 20c
Elderfield RC.King TP. J. Am. Chem. Soc. 1954, 76: 5437 - 20d
Sargent LJ. J. Org. Chem. 1956, 21: 1286 - 20e
Adib M.Tahermansouri H.Koloogani SA.Mohammadi B.Bijanzadeh HR. Tetrahedron Lett. 2006, 47: 5957 - 20f
Wang LF.Zhang HY.Kong L.Chen ZW.Shi JG. Helv. Chim. Acta 2004, 87: 1515