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

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.

SUBMITTER: Zhang L

PROVIDER: S-EPMC2888746 | biostudies-literature | 2009 Jul-Aug

REPOSITORIES: biostudies-literature

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

Zhang Li L Xiao Qing Q Ma Chao C Xie Xiang-Qun XQ Floreancig Paul E PE

Journal of combinatorial chemistry 20090701 4

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 v ...[more]

PMID: 19505108

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