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Original Articles

A CONTINUOUS PROCEDURE FOR PREPARATION OF para FUNCTION ALIZED AROMATIC THIOLS USING NEWMAN-KWART CHEMISTRY

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Pages 547-555 | Received 04 Apr 2000, Accepted 30 Aug 2000, Published online: 11 Feb 2009

REFERENCES

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  • Hagen , S. E. , VaraPrasad , J. V. N. , Boyer , F. E. , Domagala , J. M. , Ellsworth , E. L. , Gajda , C. , Hamilton , H. W. , Markoski , L. J. , Steinbaugh , B. A. , Tait , B. D. , Lunney , E. A. , Tummino , P. J. , Ferguson , D. , Hupe , D. , Nouhan , C. , Gracheck , S. J. , Saunders , J. M. and VanderRoest , S. 1997 . J. Med. Chem. , 40 : 3707
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  • Kwart , H. and Evans , E. R. 1966 . J. Org. Chem. , 31 : 410 M. S. Newman and H. A. Karnes, J. Org. Chem., 31, 3980(1966).
  • Wong , S.-C. , Sasso , S. , Jones , H. and Kaminski , J. J. 1984 . J. Med. Chem. , 27 : 20 Aldehyde groups at the para position have been used previously to activate the Newman-Kwart rearrangement.
  • Cardillo , B. , Casnati , G. and Pochini , A. 1967 . Chem. Ind. (Milan) , 49 : 630 H. Gross, A. Rieche and G. Matthey, Chem. Ber., 96, 308(1963); H. Meier, H. Kretzschmann and H. Kolshorn,. J. Org. Chem., 57, 6847 (1992); F. Dallackerand K. Wabinski-Westerop, Chem.-Ztg. 114, 144 (1990); S. Morimura, H. Horiuchi and K. Murayama, Bull. Chem. Soc. Jpn., 50, 2189(1970).
  • LC-MS analysis of impurities in CI-1029 as well as impurities in the toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxyniethyl-5-methyl-phenyl) ester (6) intermediate suggested that the hydroxymethyl group in CI-1 029 and in 6 had been converted to a carboxylic acid function in the case of the first impurity and to a N,N-dimethylcarboxamide substituent in the case of the second, more persistent impurity. This structural information led to the conclusion that the phenyl ether Newman-Kwart conditions caused formation of both impurities, and this was confirmed when we found that changing these reaction conditions as described above, allowed us to avoid both impu rities
  • Toth , J. E. and Fuchs , P. L. 1986 . J. Org. Chem. , 51 : 2594
  • Ranasinghe , M. G. and Fuchs , P. L. 1988 . Synth. Commun. , 18 : 227 J.-P. Mahieu, M. Gosselet, B. Sebille and Y. Beuzard, Bid., 16, 1709(1986)

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