1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development.

Tetrahedron

Department of Chemistry, and the Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Ave., Boston, MA 02215.

Published: June 2007

The chemistry of 1,2,3,4-tetrahydro-1,5-naphthyridines and 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines has been explored with the goal of discovering reactions at N1 suitable for library development. Epoxide openings, palladium-catalyzed N-arylations, DEPBT-promoted acylations, and urea formation through the reaction with isocyanates were all successful. The epoxide opening chemistry using homochiral epichlorohydrin, with epoxide reclosure and a second nucleophilic opening led to the preparation of a small 24-membered library.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2608727PMC
http://dx.doi.org/10.1016/j.tet.2007.04.003DOI Listing

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