The Oxidative Chlorination of Pyrimidine and Purine Bases, and Nucleosides Using Acyl Chloride-Dimethyl-Formamide-m-Chloroperbenzoic Acid System¹

References

• 1986 . A preliminary account of this work was presented at the 191st American Chemical Society National Meeting . April 13–18 1986 , New York, NY. Abstract ORGN 331.
   Google Scholar
• Fukuhara , T. K. and Visser , D. W. 1955 . J. Am. Chem. Soc. , 77 : 2393
   Web of Science ®Google Scholar
• Kikugawa , K. , Kawada , I. and Ichino , M. 1975 . Chem. Pharm. Bull. , 23 : 35
   Web of Science ®Google Scholar
• Long , R. A. , Robins , R. K. and Townsend , L. B. 1967 . J. Org. Chem. , 32 : 2751
   PubMed Web of Science ®Google Scholar
• Ikehara , M. and Kaneko , M. 1970 . Tetrahedron , 26 : 4251
   PubMed Web of Science ®Google Scholar
• Brentnall , H. J. and Hutchinson , D. W. 1972 . Tetrahedron Lett. , : 2595
   Web of Science ®Google Scholar
• Ikehara , M. , Ogiso , Y. and Maruyama , T. 1977 . Chem. Pharm. Bull. , 25 : 575
   Web of Science ®Google Scholar
• Ryu , E. K. and Malcolm , MacCoss . 1981 . J. Org. Chem. , 46 : 2819
   Web of Science ®Google Scholar
• The other chloride ion sources such as p-toluenesulfonyl chloride, phosphorous oxychloride, or phosphorous pentachloride were investigated. However, the use of acyl chloride, especially benzoyl chloride has several advantages over the other reagents described above in terms of the yields, the mild reaction conditions and the case of handling as well as facile workups.
   Google Scholar
• The use of other solvents such as dimethylacetamide (DMA) or hexa-methylphosphoramide (HMPA) gave nearly similar results in the limited experiments and no advantage over DMF.
   Google Scholar
• Dods , R. F. and Roth , J. S. 1969 . Tetrahedron Lett. , : 165
   PubMed Web of Science ®Google Scholar
• Dods , R. F. and Roth , J. S. 1969 . J. Org. Chem. , 34 : 1627
   Web of Science ®Google Scholar
• Kikugawa , K. and Ichino , M. 1972 . ibid. , 37 : 284
   Google Scholar
• Satisfactory 1H NMR and UV spectra were obtained for each product.
   Google Scholar
• Bosshard , H. H. , Mory , R. , Schmid , M. and Zollinger , Hch. 1959 . Helv. Chim. Acta. , 42 : 1653 b) ref. 11; c) ref. 12; d) ref. 13; e) H. K. Hall, Jr., J. Am. Chem. Soc., 78, 2717 (1956). f) J. Zemlicka, J. Smrt and F. Sorm, Tetrahedron Lett., 397 (1962). g) V. A. Pattison, J. G. Colson and Russell L. K. Carr, J. Org. Chem., 33, 1084 (1968). h) H. H. Bosshard und Hch. Zollinger, Helv. Chim. Acta., 42, 1659 (1959).
   Web of Science ®Google Scholar
• Barrett , H. W. , Goodman , I. and Dittmer , K. 1948 . J. Am. Chem. Soc. , 70 : 1753
   PubMed Web of Science ®Google Scholar
• Prystas , M. and Sorm , F. 1964 . Collect. Czech. Chem. Commun. , 29 : 131
   Web of Science ®Google Scholar
• Wempen , I. and Fox , J. J. 1963 . J. Med. Chem. , 6 : 688
   PubMed Web of Science ®Google Scholar
• Frisch , D. M. and Visser , D. W. 1959 . J. Am. Chem. Soc. , 81 : 1756
   Web of Science ®Google Scholar
• Robins , R. K. 1958 . J. Am. Chem. Soc. , 80 : 6671
   Web of Science ®Google Scholar
• Huang , M. , Montgomery , J. A. , Thorpe , M. C. , Stewart , E. L. , Secrist , J. A. III and Blakley , R. L. 1983 . Arch. Biochem. Biophys. , 222 : 133
   PubMed Web of Science ®Google Scholar
• Hrebabecky , H. and Beranek , J. 1978 . Collect. Czech. Chem. Commun. , 43 : 3268
   Web of Science ®Google Scholar