Abstract
The pyrimidine-2-sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl-protected 2-methyl-aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment with a thiolate. The versatility of this new nitrogen protecting group is illustrated with a new synthesis of Selegiline, a monoamine oxidase-B inhibitor marketed for the treatment of Parkinson's disease.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aziridines / chemical synthesis*
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Aziridines / chemistry
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Combinatorial Chemistry Techniques
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Copper / chemistry*
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Molecular Structure
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Monoamine Oxidase / metabolism
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Monoamine Oxidase Inhibitors / chemical synthesis*
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Monoamine Oxidase Inhibitors / chemistry
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Monoamine Oxidase Inhibitors / pharmacology*
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Organometallic Compounds / chemistry*
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Parkinson Disease / drug therapy*
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Selegiline / chemical synthesis*
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Selegiline / chemistry
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Selegiline / pharmacology
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Stereoisomerism
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Sulfhydryl Compounds / chemistry
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Sulfonamides / chemical synthesis*
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Sulfonamides / chemistry
Substances
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Aziridines
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Monoamine Oxidase Inhibitors
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Organometallic Compounds
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Sulfhydryl Compounds
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Sulfonamides
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Selegiline
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Copper
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Monoamine Oxidase