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Synthesis 2008(21): 3423-3428
DOI: 10.1055/s-0028-1083177
DOI: 10.1055/s-0028-1083177
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkMulticomponent Domino Cyclization-Oxidative Aromatization on a Bifunctional Pd/C/K-10 Catalyst: An Environmentally Benign Approach toward the Synthesis of Pyridines
Further Information
Received
23 May 2008
Publication Date:
16 October 2008 (online)
Publication History
Publication Date:
16 October 2008 (online)

Abstract
A one-pot synthesis of substituted pyridines via a domino cyclization-oxidative aromatization (dehydrogenation) approach is described. The process is based on the use of a new bifunctional noble metal-solid acid catalyst, Pd/C/K-10 montmorillonite and microwave irradiation. The cyclization readily takes place on the strong solid acid while palladium dehydrogenates the dihydropyridine intermediates to the desired products.
Key words
Pd/C/K-10 montmorillonite - solid acid - microwave irradiation - bifunctional catalysis - green chemistry - pyridines
- 1a
Hughes DL. Org. Prep. Proced. Int. 1993, 25: 607MissingFormLabel - 1b
Gilchrist TL. Heterocyclic Chemistry 3rd ed.: Addison-Wesley-Longman, Ltd.; England: 1998.MissingFormLabel - 1c
Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000, 1045MissingFormLabel - 1d
Humphrey GR.Kuethe JT. Chem. Rev. 2006, 106: 2875MissingFormLabel - 1e
Ferreira VF.De Souza MCBV.Cunha AC.Pereira LOR.Ferreira MLG. Org. Prep. Proced. Int. 2001, 33: 411MissingFormLabel - 1f
Török B.Abid M.London G.Esquibel J.Török M.Mhadgut SC.Yan P.Prakash GKS. Angew. Chem. Int. Ed. 2005, 44: 3086MissingFormLabel - 1g
Abid M.Teixeira L.Török B. Org. Lett. 2008, 10: 933MissingFormLabel - 2a
Zhang Y.Wada T.Sasabe H. Chem. Commun. 1996, 621MissingFormLabel - 2b
Somei M.Yamada F. Nat. Prod. Rep. 2004, 21: 278MissingFormLabel - 2c
Fürstner A.Szillat H.Gabor B.Mynott R. J. Am. Chem. Soc. 1998, 120: 8305MissingFormLabel - 2d
Somei M.Yamada F. Nat. Prod. Rep. 2005, 22: 73MissingFormLabel - 2e
Török M.Abid M.Mhadgut SC.Török B. Biochemistry 2006, 45: 5377MissingFormLabel - 2f
Nobuyoshi A.Akihiko O.Chikara M.Tatsuya T.Masami O.Hiromitsu S. J. Med. Chem. 1999, 42: 2946MissingFormLabel - 2g
Baran PS.Richter JM.Lin DW. Angew. Chem. Int. Ed. 2005, 44: 609MissingFormLabel - 3a
Kumar R.Mittal A.Ramachandran U. Bioorg. Med. Chem. Lett. 2007, 17: 4613MissingFormLabel - 3b
Abele E.Abele R.Lukevics E. Chem. Heterocycl. Compd. (Engl. Transl.) 2003, 39: 825MissingFormLabel - 3c
Palfreyman MN. Potassium Channels and Their Modulators Taylor and Francis; London: 1996. p.57MissingFormLabel - 3d
Bockert RH.Guengerich FP. J. Med. Chem. 1986, 29: 1596MissingFormLabel - 3e
Coburn RA.Wierzba M.Suto MJ.Solo AJ.Triggle AM.Triggle DJ. J. Med. Chem. 1988, 31: 2103MissingFormLabel - 3f
Godfraind T.Miller R.Wibo M. Pharmacol. Rev. 1986, 38: 321MissingFormLabel - 4
Spitzner D. Pyridines, In Science of Synthesis Vol. 15:Black D. Georg Thieme Verlag; Stuttgart: 2004. p.11MissingFormLabel - 5a
Hantzsch A. Justus Liebigs Ann. Chem. 1882, 215: 1MissingFormLabel - 5b
Lyle RE. In The Chemistry of Heterocyclic Compounds, Pyridine and its Derivatives Vol. 14, Suppl. Part 1:Abramovitch RA. Wiley; New York: 1974.MissingFormLabel - 5c
Stout DM.Meyers AI. Chem. Rev. 1982, 82: 223MissingFormLabel - 5d
Sausins A.Duburs G. Heterocycles 1988, 27: 269MissingFormLabel - 6a
Nasr-Esfahani M.Moghadam M.Tangestaninejad S.Mirkhani V.Momeni AR. Bioorg. Med. Chem. 2006, 14: 2720MissingFormLabel - 6b
Yadav JS.Reddy BVS.Basak AK.Baishya G.Narsaiah A.Venkat A. Synthesis 2006, 451MissingFormLabel - 6c
Panchgalle SP.Choudhary SM.Chavan SP.Kalkote UR. J. Chem. Res. 2004, 550MissingFormLabel - 6d
Tamagaki S.Mimura T.Tagaki W. J. Chem. Soc., Perkin Trans. 2 1990, 1645MissingFormLabel - 6e
Brewster ME.Simay A.Czako K.Winwood D.Farag H.Bodor N. J. Org. Chem. 1989, 54: 3721MissingFormLabel - 6f
Nakamichi N.Kawashita Y.Hayashi M. Org. Lett. 2002, 4: 3955MissingFormLabel - 6g
Fang X.Liu Y.-C.Li CJ. J. Org. Chem. 2007, 72: 8608MissingFormLabel - 7a
Augustine RL. Heterogeneous Catalysis for the Synthetic Chemist Marcel Dekker; New York: 1996.MissingFormLabel - 7b
Smith GV.Notheisz F. Heterogeneous Catalysis in Organic Chemistry Academic Press; San Diego: 1999.MissingFormLabel - 8a
Corma A. Chem. Rev. 1995, 95: 559MissingFormLabel - 8b
Gates BC. Catalysis by Solid Acids, In Encyclopedia of Catalysis Vol. 2:Horváth I. Wiley; New York: 2003. p.104MissingFormLabel - 8c
Yip ACK.Lam FLY.Hu XJ. Chem. Commun. 2005, 3218MissingFormLabel - 8d
Molnár . Curr. Org. Chem. 2008, 12: 159MissingFormLabel - 9a
Stereochemistry of Heterogeneous Metal Catalysis
Bartók M. Wiley; Chichester: 1985.MissingFormLabel - 9b
Bartók M.Molnár . Heterogeneous Catalytic Hydrogenation, In Chemistry of Functional GroupsPatai S. Wiley; Chichester: 1997. Suppl. A3, Chap. 16. p.843MissingFormLabel - 10a
Varma RS.Dahiya R.Kumar S. Tetrahedron Lett. 1997, 38: 2039MissingFormLabel - 10b
Walla P.Kappe CO. Chem. Commun. 2004, 5: 594MissingFormLabel - 10c
Loupy A. Microwaves in Organic Synthesis Wiley-VCH; Weinheim: 2005.MissingFormLabel - 10d
Kappe CO.Stadler A. Microwaves in Organic and Medicinal Chemistry Wiley-VCH; Weinheim: 2005.MissingFormLabel - 10e
Kappe CO.Dallinger D. Nature Rev. 2006, 5: 51MissingFormLabel - 11a
Szöllösi G.Török B.Baranyi L.Bartók M. J. Catal. 1998, 179: 619MissingFormLabel - 11b
Török B.London G.Bartók M. Synlett 2000, 631MissingFormLabel - 11c
Landge SM.Schmidt A.Outerbridge V.Török B. Synlett 2007, 1600MissingFormLabel - 12a
Abid M.Török B. Adv. Synth. Catal. 2005, 347: 1797MissingFormLabel - 12b
Abid M.Landge SM.Török B. Org. Prep. Proced. Int. 2006, 35: 495MissingFormLabel - 12c
Abid M.Spaeth A.Török B. Adv. Synth. Catal. 2006, 348: 2191MissingFormLabel - 12d
Landge SM.Atanassova V.Thimmaiah M.Török B. Tetrahedron Lett. 2007, 48: 5161MissingFormLabel - 12e
Abid M.De Paolis O.Török B. Synlett 2008, 410MissingFormLabel - 12f
Landge SM.Berryman M.Török B. Tetrahedron Lett. 2008, 49: 4505MissingFormLabel - 13a
Theng BKG. The Chemistry of Clay-Organic Reactions Halsted Press (a Wiley division); New York: 1974.MissingFormLabel - 13b
Benesi HA.Winquest BHC. Adv. Catal. 1978, 27: 97MissingFormLabel - 13c
Balogh M.Laszlo P. Organic Chemistry Using Clays Springer-Verlag; Berlin/Heidelberg: 1993.MissingFormLabel - 13d
Cseri T.Békássy S.Figueras F.Cseke F.de Ménorval L.-C.Dutatre R. Appl. Catal. A 1995, 132: 141MissingFormLabel - 13e
Vaccari A. Appl. Clay Sci. 1999, 14: 161MissingFormLabel - 13f
Nikalje MD.Phukan P.Sudalai A. Org. Prep. Proced. Int. 2000, 32: 1MissingFormLabel - 13g
Varma RS. Tetrahedron 2002, 58: 1235MissingFormLabel - 13h
Dasgupta S.Török B. Org. Prep. Proced. Int. 2008, 40: 1MissingFormLabel - 14
Török B.Prakash GKS. Adv. Synth. Catal. 2003, 345: 165