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J Comb Chem. 2009 Jul-Aug;11(4):640-4. doi: 10.1021/cc800200h.

Construction of a bicyclic beta-benzyloxy and beta-hydroxy amide library through a multicomponent cyclization reaction.

Author information

1
University of Pittsburgh Center for Chemical Methodologies and Library Development and Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.

Abstract

In this manuscript, we describe the synthesis of a bicyclic beta-benzyloxy and beta-hydroxy amide library from cyanohydrin ethers. The benzyloxy amides were prepared through a one-pot sequence of hydrozirconation, acylation, and intramolecular Friedel-Crafts alkylation. Selected benzyl ethers were converted to alcohols by hydrogenolysis in a continuous flow reactor. Chemistry space BCUT metrics and 2D fingerprint similarity calculations showed that these compounds contribute chemical diversity value to existing chemical libraries.

PMID:
19505108
PMCID:
PMC2888746
DOI:
10.1021/cc800200h
[Indexed for MEDLINE]
Free PMC Article

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