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

…, M Palucki, L Tan, N Yasuda, DL Hughes…

Index: 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 Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8723 - 8730

Full Text: HTML

Citation Number: 30

Abstract

The preparation of 3-(5, 6, 7, 8-tetrahydro-1, 8-naphthyridin-2-yl) propan-1-amine 2a and 3- [(7 R)-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'- ...