Abstract
The Pd(II)-catalyzed intramolecular oxidative cyclization of tosyl-protected cis- and trans-N-allyl-2-aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane-fused pyrimidin-4-ones and 1,5-diazocin-6-ones were developed. In the course of the research, a marked solvent effect was observed on both the regio- and diastereoselectivity. Additionally, a novel Pd(II)-mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis-aminopalladation mechanism.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Allyl Compounds / chemistry*
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Amination
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Azocines / chemical synthesis*
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Azocines / chemistry
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Catalysis
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Cyclization
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Cyclohexanecarboxylic Acids / chemical synthesis*
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Cyclohexanecarboxylic Acids / chemistry
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Cyclohexanes / chemical synthesis*
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Cyclohexanes / chemistry
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Cyclohexylamines / chemical synthesis*
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Cyclohexylamines / chemistry
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Molecular Structure
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Oxidation-Reduction
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Palladium / chemistry*
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Pyrimidinones / chemical synthesis*
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Pyrimidinones / chemistry
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Stereoisomerism
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Vinyl Compounds / chemical synthesis*
Substances
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Allyl Compounds
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Azocines
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Cyclohexanecarboxylic Acids
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Cyclohexanes
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Cyclohexylamines
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Pyrimidinones
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Vinyl Compounds
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2-aminocyclohexanecarboxylic acid
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Palladium