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Solution-phase parallel synthesis of a multisubstituted cyclic imidate library.

ABSTRACT: The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative amidation, and Heck chemistry using sublibraries of commercially available building blocks.

SUBMITTER: Mehta S

PROVIDER: S-EPMC3740045 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Solution-phase parallel synthesis of a multisubstituted cyclic imidate library.

Mehta Saurabh S Waldo Jesse P JP Neuenswander Benjamin B Lushington Gerald H GH Larock Richard C RC

ACS combinatorial science 20130404 5

The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative ami ...[more]

PMID: 23514214

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