Solid-phase syntheses of 1,2,4-trisubstituted urazole and thiourazole derivatives

Journal of Combinatorial Chemistry

Volumn 4, Issue 5, 2002, Pages 491-495

  Phoon, Chee Wee ^a   Sim, Mui Mui ^a  

^a INSTITUTE OF MOLECULAR AND CELL BIOLOGY   (Singapore)

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ARTICLE;

EID: 0012935339     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0200134     Document Type: Article

References (25)

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19. 3): δ 69.2, 116.5, 130.1, 136.5.
20. For substitution by hydrazine without the use of DMAP, see the following. Lee, A.; Huang, L.; Ellman, J. A. General Solid-Phase Method for the Preparation of Mechanism-Based Cysteine Protease Inhibitors. J. Am. Chem. Soc. 1999, 121, 9907-9914.
21. The displacement was confirmed by the disappearance of all the peaks of the imidazole group and the existence of peaks associated with the diisopropylhydrazine moiety at δ 20.1, 21.2, 50.0, 51.0.
22. 1H NMR signals identical to the signals of the authentic sample available commercially (Sigma-Aldrich Rare Chemicals). The above procedure was repeated with a smaller amount of resin (33 mg) and gave the diisopropylhydrazine monohydrochloride (1.9 mg). On the basis of the initial loading of Wang resin (0.76 mmol/g) as specified by the supplier, the average loading of diisopropylhydrazine resin was calculated to be 54%.
23. 2Ph), 66.8, 70.1.
24. 3.
25. Mass spectrometry of the crude cyclized mixture did not detect any iodo-containing urazole, indicating that all of the iodo groups had been reacted during the Suzuki reaction.