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Synthesis of benzyl substituted naphthalenes from benzylidene tetralones.

ABSTRACT: A convenient and efficient synthesis of novel highly substituted dimethoxybenzylnaphthalenes, which are precursors to several dihydroxynaphthoic acids, is described. The approach involves the use of aldol chemistry to provide a number of benzylidene tetralones, which are converted to the target naphthalenes in three steps, with good to excellent yields. Grignard reaction of intermediate benzyl tetralones provided 1-substituted benzyl naphthalenes. The reported synthesis is flexible and scalable and provides access to naphthalenes having a variety of substitution patterns. These benzyl substituted naphthalenes are being converted to naphthoic acids and the bioactivities of these compounds are currently being investigated.

SUBMITTER: Deck LM

PROVIDER: S-EPMC3686124 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Synthesis of benzyl substituted naphthalenes from benzylidene tetralones.

Deck Lorraine M LM Mgani Quintino Q Martinez Andrea A Martinic Alice A Whalen Lisa J LJ Vander Jagt David L DL Royer Robert E RE

Tetrahedron letters 20120101 4

A convenient and efficient synthesis of novel highly substituted dimethoxybenzylnaphthalenes, which are precursors to several dihydroxynaphthoic acids, is described. The approach involves the use of aldol chemistry to provide a number of benzylidene tetralones, which are converted to the target naphthalenes in three steps, with good to excellent yields. Grignard reaction of intermediate benzyl tetralones provided 1-substituted benzyl naphthalenes. The reported synthesis is flexible and scalable ...[more]

PMID: 23794758

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