New Methods and Reagents in Organic Synthesis. 34. Diphenyl Phosphorazidate (DPPA) as a 1,3-Dipole. A Simple, Efficient Conversion of Akyl Phenyl Ketones to 2-Phenylalkanoic Acids

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概要

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• Propiophenone (11) was conveniently converted to its enamines 12a-c using boron trifluoride etherate as a catalyst. Reaction of diphenyl phosphorazidate (DPPA) with the enamines 12a-c efficiently afforded the N-phosphorylated amidines 14a-c by the 1,3-dipolar cycloaddition of DPPA to the enamine double bond, followed by the evolution of nitrogen from the intermediate triazoline 13,and 1,2-migration of the phenyl group. 1,3-Dipolar dlimination products 15a-c were also formed, though in very low yields. Some chemical properties of the N-phosphorylated amidine 14a, as well as the 1,3-dipolar character of DPPA, were investigated. By the same reaction sequences (enamine formation followed by the 1,3-dipolar cycloaddition of DPPA), some alkyl phenyl ketones 29a-c were conveniently converted to the N-phosphorylated amidines 31a, 31b, and 27 via the enamines 30a-c. However, in the case of acetophenone and its derivatives 33a-c, these reaction sequences proceeded sluggishly. Alkaline hydrolysis of the N-phosphorylated amidines 14a, 31a, 31b, and 27 with potassium hydroxide afforded 2-phenylalkanoic acids 25 and 32a-c, respectively, in excellent yields. The overall three-step process of successive treatment of alkyl phenyl ketones (alkyl〓methyl) with pyrrolidine, DPPA, and potassium hydroxide may provide a new general method for the efficient conversion of alkyl aryl ketones to 2-arylalkanoic acids.

• 公益社団法人日本薬学会の論文
• 1983-08-25

著者

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 塩入 孝之

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 河合 伸高

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 河合 伸高

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)central Research Laboratorie

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