Abstract
The sequential one-pot double dearomatization of bis(N-benzyl-P,P-diphenylphosphinamides) via anionic cyclization is described for the first time. Protonation and alkylation of the dearomatized dianions provide bis(tetrahydro-2,1-benzazaphospholes) in good yield and with very high regio- and stereocontrol. Acid-catalyzed methanolysis of the bisheterocycles affords bis(methyl gamma-aminophosphinates) stereospecifically. The doubly phosphorylated systems proved to be active against a series of cancer cell lines.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemical synthesis
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Amides / chemistry*
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Amides / toxicity*
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Anions / chemistry*
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / toxicity*
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Aza Compounds / chemistry
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Cell Line, Tumor
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Cell Survival / drug effects
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Cyclization
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Humans
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Phosphines / chemistry*
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Structure-Activity Relationship
Substances
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Amides
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Anions
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Antineoplastic Agents
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Aza Compounds
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Phosphines