Double Dearomatization of Bis(diphenylphosphinamides) through Anionic Cyclization. A Facile Route of Accessing Multifunctional Systems with Antitumor Properties

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• 作者：Gloria Ruiz-G&oacute ; mez ; Marí ; a José ; Iglesias ; Manuel Serrano-Ruiz ; Santiago Garcí ; a-Granda ; André ; s Francesch ; Fernando L&oacute ; pez-Ortiz ; Carmen Cuevas
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：May 11, 2007
• 年：2007
• 卷：72
• 期：10
• 页码：3790 - 3799
• 全文大小：229K
• 年卷期：v.72,no.10(May 11, 2007)
• ISSN：1520-6904

文摘

The sequential one-pot double dearomatization of bis(N-benzyl-P,P-diphenylphosphinamides) via anioniccyclization is described for the first time. Protonation and alkylation of the dearomatized dianions providebis(tetrahydro-2,1-benzazaphospholes) in good yield and with very high regio- and stereocontrol. Acid-catalyzed methanolysis of the bisheterocycles affords bis(methyl -aminophosphinates) stereospecifically.The doubly phosphorylated systems proved to be active against a series of cancer cell lines.