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Synthesis 2012(11): 1614-1624
DOI: 10.1055/s-0031-1289714
DOI: 10.1055/s-0031-1289714
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
Efficient Preparation of Tetrasubstituted Pyrazines Starting from Pyrazin-2(1H)-ones
Further Information
Received
4 January 2012
Publication Date:
16 February 2012 (online)
Publication History
Publication Date:
16 February 2012 (online)
Abstract
An efficient methodology for the synthesis of tetrasubstituted pyrazines starting from pyrazin-2(1H)-ones has been elaborated. Diversity in the functionalization and the beneficial effect of microwave irradiation throughout the methodology has been demonstrated.
Key words
palladium catalysis - copper catalysis - pyrazines - 3,5-dichloropyrazin-2(1H)-ones - microwaves - nucleosides
-
1a
Koehler PE.Odell GV. J. Agric. Food Chem. 1970, 18: 895 -
1b
Maga JA.Sizer CE. J. Agric. Food Chem. 1973, 21: 22 -
1c
Mega JA. Pyrazines in Food. An Update, In Critical Reviews in Food Sciences and Nutrition Vol. 16:Furia TE. CRC; Boca Raton FL: 1982. p.1-48 -
1d
Leunissen M.Davidson VJ.Kakuda Y. J. Agric. Food Chem. 1996, 44: 2694 -
1e
Wailzer B.Klocker J.Buchbauer G.Ecker G.Wolschann P. J. Med. Chem. 2001, 44: 2805 -
1f
Barlin GB. The Chemistry of Heterocyclic Compounds Vol. 41: Wiley; New York: 1982. -
1g
Walker JA.Liu W.Wise DS.Drach JC.Townsend LB. J. Med. Chem. 1998, 41: 1236 -
1h
De Clercq E. Med. Res. Rev. 2010, 30: 667 -
2a
Ohta A.Itoh R.Kaneko Y.Koike H.Yuasa K. Heterocycles 1989, 29: 939 -
2b
Buchi G.Galindo J.
J. Org. Chem. 1991, 56: 2605 -
2c
Heathcock CH.Smith SC. J. Org. Chem. 1994, 59: 6828 -
2d
Drogemuller M.Flessner T.Jautelat R.Scholz U.Winterfeldt E. Eur. J. Org. Chem. 1998, 2811 -
2e
McCullough KJ. In Rodd’s Chemistry of Carbon Compounds 2nd ed., Vol. 4, Parts I-J:Sainsbury M. Elsevier; Amsterdam: 2000. p.99 -
2f
Elmaaty TA.Castle LW. Org. Lett. 2005, 7: 5529 -
2g
Aparicio D.Attanasi OA.Filippone P.Ignacio R.Lillini S.Mantellini F.Palacios F.de los Santos JM.
J. Org. Chem. 2006, 61: 5897 -
2h
Taber DF.DeMatteo PW.Taluskie KV. J. Org. Chem. 2007, 62: 1492 -
2i
Candelon N.Shinkaruk S.Bennetau B.Bennetau-Pelissero C.Dumartin M.-L.Degueil M.Babin P. Tetrahedron 2010, 66: 2463 - 3
Topics in Heterocyclic Chemistry
Vol.
1:
Van der Eycken E.Kappe CO. Springer; Berlin: 2006. p.267 - 4
Modha SG.Trivedy JC.Mehta VP.Ermolat’ev DS.Van der Eycken EV. J. Org. Chem. 2011, 76: 846 - 5
Mehta VP.Modha SG.Ermolate’ev D.Van Hecke K.Van Meervelt L.Van der Eycken EV. Aust. J. Chem. 2009, 62: 27 - 6
Mehta VP.Sharma A.Van Hecke K.Van Meervelt L.Van der Eycken E. J. Org. Chem. 2008, 73: 2382 - 7
Molina P.Alajarin M.Fresneda PM.Lidon MJ.Vilaplana MJ. Synthesis 1982, 598 - 8
Singh BK.Parmar VS.Van der Eycken E. Synlett 2008, 3021 -
9a
Stimac A.Kobe J. Carbohydr. Res. 2000, 324: 149 -
9b
Stimac A.Kobe J. Carbohydr. Res. 2000, 329: 317 - 10
Ankati H.Biehl E. Tetrahedron Lett. 2009, 50: 4677 - 11
Mehta VP.Modha SG.Van der Eycken E. J. Org. Chem. 2008, 73: 976