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

ABSTRACT: 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.

SUBMITTER: Woo GH

PROVIDER: S-EPMC2608727 | biostudies-literature | 2007 Jun

REPOSITORIES: biostudies-literature

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

Woo Grace H C GH Beeler Aaron B AB Snyder John K JK

Tetrahedron 20070601 25

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 ...[more]

PMID: 19112520

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