N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides

Tetrahedron

Volumn 52, Issue 28, 1996, Pages 9347-9366

  Barton, Derek H R ^a   Ferreira, J Albert ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; PYRIDINOL; SULFENAMIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; RESIDUE ANALYSIS;

EID: 0030575364     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00487-5     Document Type: Article

References (64)

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4. 3. See, for example : Barton, D. H. R., Jaszberenyi, J. Cs., Theodorakis, E. A., Reibenspies, J. H. J. Am. Chem. Soc. 1993, 115, 8050-8059 and the many references there cited.
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9. 6. Beckwith, A. L. J. in "The Chemistry of Amides", Ed. J. Zabicky, Interscience Publishers (London), 1970, Chapter 2, pp. 73-185; Challis, B. C. and Challis, J. A. in "Comprehensive Organic Chemistry", Eds. D. H. R. Barton and W. D. Ollis, Pergamon Press (Oxford), 1979, Volume 2, Chapter 9.9, pp. 957-986.
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23. 19. This augurs well for a non-radical mechanism. It should, however, be noted that radical processes can be triggered by means other than heating or irradiation (for an example of a radical reaction catalyzed by oxygen, see : Barton, D. H. R., Bridon, D., Zard, S. Z. Tetrahedron Lett. 1986, 27, 4309-4312). We did, of course, verify that a radical trap (TEMPO) does not influence the distribution of products under the standard reaction conditions (cf. Experimental Section).
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26. 21. See, also : Tavs, P. Angew. Chem. Int. Ed. Engl. 1966, 5, 1048-1049 and Davis, F. A., Skibo, E. B. J. Org. Chem. 1976, 41, 1333-1336.
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29. 23. Barton, D. H. R., Samadi, M. Tetrahedron 1992, 48, 7083-7090; For a recent article on the use of the thallium(I) salt of N-hydroxypyridine-2(1H)-thione, see : Aveline, B. M., Kochevar, I. E., Redmond, R. W. J. Am. Chem. Soc. 1995, 117, 9699-9708.
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32. 25. We prefer our method involving the use of 2,2′-dithiodipyridine-1,1′-dioxide and a tervalent phosphine for the generation of transient Barton PTOC esters (see the article directly following).
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43. 35. N-Hydroxypyridine-2(1H)-thione can be purchased as the sodium salt "Sodium Omadine®" from the Olin Corporation. The free acid is readily obtained on acidification with HCl : Shaw, E., Bernstein, J., Losee, K., Lott, W. A. J. Am. Chem. Soc. 1950, 72, 4362-4364; See also : Barton, D. H. R., Bridon, D., Fernandez-Picot, I., Zard, S. Z. Tetrahedron 1987, 43, 2733-2740.
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