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Synthesis 2010(20): 3429-3432
DOI: 10.1055/s-0030-1258212
DOI: 10.1055/s-0030-1258212
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Facile and Green Synthesis of a Naphthyridine Derivative: A Novel Hedgehog Pathway Modulator
Weitere Informationen
Received
6 May 2010
Publikationsdatum:
13. August 2010 (online)
Publikationsverlauf
Publikationsdatum:
13. August 2010 (online)
Abstract
A green and highly efficient synthesis of a naphthyridine derivative, a novel hedgehog pathway modulator, in high yield and purity from inexpensive starting materials is described. The key step involves an acid-promoted aryl amination reaction of aniline with naphthyridine halides.
Key words
aryl amination - acid-promoted coupling - green chemistry - naphthyridine - pyridine cyclization
-
1a
Xie J. Curr. Oncol. Rep. 2008, 10: 107 -
1b
Xie J. Future Oncol. 2005, 1: 331 -
2a
Kumar SK.Roy I.Anchoori RK.Fazli S.Maitra A.Beachy PA.Khan SR. Bioorg. Med. Chem. 2008, 16: 2764 -
2b
Levitt RJ.Zhao Y.Blouin M.-J.Pollak M. Cancer Lett. 2007, 255: 300 -
2c
Chen JK.Taipale J.Young KE.Maiti T.Beachy PA. Proc. Natl. Acad. Sci. U.S.A. 2002, 99: 14071 - 3
Cheng D,Han D,Gao W,Jiang J,Pan S, andWan Y. inventors; Patent WO 2008014291. ; Chem. Abstr. 2008, 148, 191938 - 4
Singh B.Lesher GY.Brundage RP. Synthesis 1991, 894 - 5
Bredereck H.Effenberger F.Botsch H. Chem. Ber. 1964, 97: 3397 - For recent reviews on Buchwald-Hartwig aryl amination reactions, see:
-
6a
Mauger CC.Mignani GA. Aldrichimica Acta 2006, 39: 17 -
6b
Schlummer B.Scholz U. Adv. Synth. Catal. 2004, 346: 1599 - 6c Frost C. G., Mendonça P.; J. Chem. Soc., Perkin Trans. 1; 1998, 2615
- For articles on palladium-catalyzed aryl amination of heteroaromatic compounds with morpholine or aniline, see:
-
7a
Navarro O.Marion N.Mei J.Nolan SP. Chem. Eur. J. 2006, 12: 5142 -
7b
Tewari A.Hein M.Zapf A.Beller M. Tetrahedron 2005, 61: 9705