Methods for the Synthesis of 5,6,7,8-Tetrahydro-1,8-naphthyridine Fragments for αVβ3 Integrin Antagonists

The preparation of 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine 2a and 3-[(7R)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]propan-1-amine 2b, key intermediates in the synthesis of αVβ3 antagonists, is described. The syntheses rely on the efficient double Sonogashira reactions of...

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Veröffentlicht in:	Journal of organic chemistry 2004-12, Vol.69 (25), p.8723-8730
Hauptverfasser:	Hartner, Frederick W, Hsiao, Yi, Eng, Kan K, Rivera, Nelo R, Palucki, Michael, Tan, Lushi, Yasuda, Nobuyoshi, Hughes, David L, Weissman, Steven, Zewge, Daniel, King, Tony, Tschaen, Dave, Volante, R. P
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties
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Zusammenfassung:	The preparation of 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine 2a and 3-[(7R)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]propan-1-amine 2b, key intermediates in the synthesis of αVβ3 antagonists, is described. The syntheses rely on the efficient double Sonogashira reactions of 2,5-dibromopyridine 3 with acetylenic alcohols 4a/4b and protected propargylamines 10a−e followed by Chichibabin cyclizations of 3,3‘-pyridine-2,5-diyldipropan-1-amines 9a/9b.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0486950