| Dearomatizing anionic cyclization of N-alkyl-N-benzyl(dinaphthyl)phosphinamides. A facile route to gamma-(amino)dihydronaphthalenylphosphinic acids. | |
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MedLine Citation:
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PMID: 17979287 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The dearomatizing anionic cyclization of N-alkyl-N-benzyldi(n-naphthyl)phosphinamides (n = 1, 2) and subsequent trapping with a series of electrophiles (MeOH, MeI, CF3SO3Me, Me3O+BF4-, AllylBr, and PhCH2Br) have been accomplished. Optimized reaction conditions (base, temperature, reaction time) allow for synthesizing tetrahydro-1H-naphtho[1,2-c][1,2]-azaphosphole 1-oxides 13 and 18 and tetrahydro-1H-naphtho[2,1-c][1,2]azaphosphole 3-oxides 16 and 27-29 in high yield and diastereoselectivity. Appropriate selection of the base proved to be critical for promoting anionic cyclization of 2-naphthyl derivatives. The dearomatized heterocycles are transformed quantitatively into gamma-(N-alkylamino)phosphinic acids by acid hydrolysis of the P-N linkage. Bioactivity assays on five human tumor cell lines for one of these amino acids revealed growth inhibition factors (GI50) at a micromolar scale. Additionally, evidence for the feasibility of intermolecular nucleophilic dearomatization and sequential nucleophilic attack to both aromatic rings of dinaphthylphosphinamides have been obtained. |
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Authors:
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Gloria Ruiz-Gómez; María José Iglesias; Manuel Serrano-Ruiz; Fernando López-Ortiz |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2007-11-03 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Dec |
Date Detail:
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Created Date: 2007-11-30 Completed Date: 2008-02-20 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 9704-12 Citation Subset: IM |
Affiliation:
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Area de Química Orgánica, Universidad de Almería, Carretera de Sacramento, 04120 Almería, Spain. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amides
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chemical synthesis*,
chemistry,
pharmacology Antineoplastic Agents / chemical synthesis*, chemistry, pharmacology Cell Line, Tumor Cell Proliferation / drug effects Cyclization Drug Screening Assays, Antitumor Humans Molecular Conformation Organophosphorus Compounds / chemical synthesis*, chemistry, pharmacology Phosphinic Acids / chemical synthesis*, chemistry, pharmacology Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Amides; 0/Antineoplastic Agents; 0/Organophosphorus Compounds; 0/Phosphinic Acids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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