A New Synthesis of Some Non-Steroidal Anti-Inflammatory Agents via Cyanophosphates¹)

References

• Kato , N. , Hamada , Y. and Shioiri , T. 1984 . Chem, Pharm. Bull. , 32 : 1679 This paper constitutes Part 45 of a series of papers entitled “New Methods and Reagents in Organic Synthesis”. For Part 44
   Web of Science ®Google Scholar
• Harusawa , S. , Yoneda , R. , Kurihara , T. , Hamada , Y. and Shioiri , T. 1984 . Tetrahedron Lett. , 25 : 427
   Web of Science ®Google Scholar
• Harusawa , S. , Hamada , Y. and Shioiri , T. 1979 . Synthesis Diethyl phosphorocyanidate has been extensively utilized as a versatile reagent for cyanation under mild and non-aqueous conditions. a), 716.
   Google Scholar
• Harusawa , S. , Hamada , Y. and Shioiri , T. 1979 . Tetrahedron Lett. 4663.
   Google Scholar
• Ishida , T. , Inoue , M. , Harusawa , S. , Hamada , Y. and Shioiri , T. 1981 . Acta Crystallogr., Sect. B , 37 : 1881
   Web of Science ®Google Scholar
• Harusawa , S. , Hamada , Y. and Shioiri , T. 1981 . Heterocycles , 15 : 981
   Web of Science ®Google Scholar
• Harusawa , S. and Shioiri , T. 1982 . Tetrahedron Lett. , 22 : 447
   Web of Science ®Google Scholar
• Harusawa , S. , Yoneda , R. , Kurihara , T. , Hamada , Y. and Shioiri , T. 1983 . Chem. Pharm. Bull. , 31 : 2932
   Web of Science ®Google Scholar
• Baldwin , J. E. , Barton , D. H. R. , Dainis , I. and Pereira , J. L. C. 1968 . J. Chem. Soc. (C) , Several procedures are available for the conversion of carbonyl group to nitrile containing one additional carbon atom, a), 2283.In the case of benzopenone and α-tetralone, the corresponding cyanohydrins are not formed by this procedure
   Google Scholar
• Oldenziel , O. H. and van Leusen , A. M. 1973 . Tetrahedron Lett. 1357.
   Google Scholar
• Oldenziel , O. H. , van Leusen , D. and van Leusen , A. M. 1977 . J. Org. Chem. , 42 : 3114
   Web of Science ®Google Scholar
• van Leusen , A. M. and Oomkes , P. G. 1980 . Synth. Commun. , : 399
   Web of Science ®Google Scholar
• Orere , D. M. and Reese , C. B. 1977 . J. Chem. Soc., Chem. Commun. , 280.
   Google Scholar
• Jiricny , J. , Orere , D. M. and Reese , C. B. 1980 . J. Chem. Soc., Perkin. Trans. , 1 1487.
   Google Scholar
• Belletire , J. L. 1982 . Synth. Commun. , : 763 Belletire has recently reported that trimethylsilyloxy nitriles, prepared from aryl ketones, give arylacetic acids by stannous chloride, acetic acid, and concentrated hydrochloric acid under refluxing conditions.
   Web of Science ®Google Scholar
• Lednicer , D. and Mitscher , L. A. 1977 . “ 6 ” . In The Organic Chemistry of Drug Synthesis , Vol. 1 , New York : John Wiley and Sons . For reviews on the preparation of these drugs, see, “” Chapter; idem, ibid.Vol. 21980, Chapter 4
   Google Scholar
• Adams , S. S. , Cliffe , E. E. , Lessel , B. and Nicholson , J. S. 1967 . J. Pharm. Sci. , 56 : 1686
   PubMed Web of Science ®Google Scholar
• Harrison , I. T. , Lewis , B. , Nelson , P. , Rooks , W. , Roszkowski , A. , Tomolonis , A. and Fried , J. H. 1970 . J. Med. Chem. , 13 : 203 J. Riegel, M. L. Maddox, and I. T. Harrison, ibid., 17, 377 (1974).
   PubMed Web of Science ®Google Scholar
• Juby , P. F. , Goodwin , W. R. , Hudyma , T. W. and Partyka , R. A. 1972 . J. Med. Chem. , 15 : 1297 b) The Merck Index10th Edition 2319(1983.
   PubMed Web of Science ®Google Scholar
• 1977 . Japan Patent , a) Sankyo Co., Ltd.,38906.
   Google Scholar
• Misaka , E. , Yamaguchi , T. , Iizuka , Y. , Kamoshida , K. , Kojima , T. , Kobayashi , K. , Endo , Y. , Misawa , Y. , Kobayashi , S. and Tanaka , K. 1981 . Oyo Yakuri , 21 : 753
   Google Scholar
• Matsuda , K. , Ohnishi , K. , Sha , T. , Yamazaki , M. , Tanaka , Y. and Tanaka , K. 1982 . Jpn. J. Inflamm. , 2 : 263
   Google Scholar
• Naruto , S. and Terada , A. 1983 . Chem. Pharm. Bull. , 31 : 4286
   Web of Science ®Google Scholar
• Naruto , S. and Terada , A. 1983 . ibid. , 31 : 4319
   Google Scholar
• Naruto , S. , Tanaka , Y. , Hayashi , R. and Terada , A. 1984 . ibid. , 32 : 258
   Google Scholar
• Nicholson , J. S. and Adams , S. S. 1966 . Nicholson and Adams have reported an alternative method for the synthesis of ibuprofen by treatment of cyanohydrin derived from acetophenone with hydrogen iodide and red phosphorus, but it is not clear on its details., U. S. Patent 3,228,831.
   Google Scholar