Solid-phase syntheses of heterocycles containing the 2-aminothiophenol moiety

Journal of Combinatorial Chemistry

Volumn 2, Issue 3, 2000, Pages 282-292

  Yokum, T Scott ^a   Alsina, Jordi ^a   Barany, George ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOTHIOPHENOL; 2-AMINOTHIOPHENOL; ANILINE DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANILINE COMPOUNDS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY;

EID: 0034181916     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9900854     Document Type: Article

References (48)

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2. Portions of this work were reported in preliminary form: (a) Sixteenth American Peptide Symposium, Minneapolis, Minnesota, June 26-July 1, 1999: Yokum, T. S.; Alsina, J.; Barany, G. In Peptides for the New Millennium: Proceedings of the 16th American Peptide Symposium; Fields, G. B., Tam, J. P., Barany, G., Eds.; Kluwer: Dordrecht, The Netherlands, 2000, pp 196-197.
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27. A similar reaction has been described for the synthesis of benzimidazoles. See: ref 4b.
28. The use of excess DDQ resulted in unacceptable levels of side products, as revealed by HPLC analysis.
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30. Alternative stepwise procedures for the generation of the core structures were also investigated: (a) alkylation of 6 with free sulfhydryl (after S-trityl removal) by an α-bromo ketone, followed by reduction of the nitro group, and finally reductive amination; and (b) reductive amination of an α-bromo ketone onto S-trityl protected 7, trityl deprotection, and finally treatment with base. These procedures were far inferior to the one-pot method; at most 50% product formed according to HPLC analysis, and in some cases, no product formed.
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38. 3,4-Dihydro-3-oxo-1,4-benzothiazines have been prepared in solution using similar procedures. See: (a) Funke, A.; Funke, G.; Millet, B. Dérivés de la phényl-2-dihydro-2,3-benzothiazine-1,4. Bull. Soc. Chim. Fr. 1961, 1524-1526.
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41. Many alternative solution-phase routes to 3,4-dihydro-3-oxo-1,4-benzothiazines have been reported and reviewed in ref 3b.
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47. For corresponding experiments using Wang-glycine resin, 1.04 g (0.77 mmol/g, 0.80 mmol) was used.
48. For corresponding experiments using resin with the substrate bound to glycine, 43.1 mg (0.58 mmol/g, 0.025 mmol) was used.