NDLI: Synthesis of Substituted Imidazo[1,2-h][1,7]naphthyridines as H+/K+-ATPase Inhibiting Drug Precursors via Directedortho-Metalation of Imidazo[1,2-a]pyridines

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Synthesis of Substituted Imidazo[1,2-h][1,7]naphthyridines as H+/K+-ATPase Inhibiting Drug Precursors via Directedortho-Metalation of Imidazo[1,2-a]pyridines

Content Provider	Scilit
Author	Senn-Bilfinger, Jörg Kohl, Bernhard Rainer, Georg Buhr, Wilm Holst, Hans Christof Zimmermann, Peter Jan
Copyright Year	2008
Description	Selective directed ortho-metalation (DOM) of 2,3-dimethyl-8-(pivaloylamino)imidazo[1,2-a]pyridine in the 7-position was achieved with tert-butyllithium. Subsequent reaction of the lithiated derivative with tributylchlorostannane to the corresponding 7-trialkylstannyl analogue and palladium-catalyzed Stille acylation with 3-arylpropenoic acid chlorides in the presence of lithium chloride gave the corresponding 7-acylated imidazopyridines in good yields. Cyclization to the target imidazonaphthyridines, which are precursors in the synthesis of gastric $H^{+}/K^{+}$-ATPase inhibiting drugs, was achieved by treatment with strong acid. For scaled-up production of 2,3-dimethyl-9-phenyl-9,10-dihydroimidazo[1,2-h][1,7]naphthyridin-7(8H)-one, a tin-free process has been developed. Accordingly, the 7-lithiated 2,3-dimethyl-8-(pivaloylamino)imidazo[1,2-a]pyridine was reacted directly with cinnamaldehyde and the resultant alcohol oxidized with manganese dioxide to give the unsaturated 7-acylated imidazopyridine.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2008-1067264.pdf
Ending Page	3070
Page Count	6
Starting Page	3065
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-2008-1067264
Journal	Synthesis
Issue Number	19
Volume Number	2008
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2008-09-05
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Directed Ortho-metalation
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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