Convenient one-pot formation of highly functionalized 5-halothiazoles

Eduard Dolusic, Sara Modaffari, Lionel Pochet, Johan Wouters, Bernard Masereel, Raphael Frédérick

Research output: Contribution to conferencePoster

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Abstract

Attempts to synthesize substituted thiazole N-oxides by treatment of 1,3-thiazoles with mCPBA(1,2) did not afford the expected products. Spectral analyses proved that corresponding 5-bromothiazoles were formed instead in very good yields. This can be explained by the fact that the starting compounds were, in fact, obtained as hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents in the 4-position and on the 2-nitrogen could be easily prepared by this rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or hazardous reagents like elemental bromine. A number of oxidants, solvents and reaction conditions were next studied. The synthesis scope was successfully extended to 5-chlorothiazoles. Attempts were undertaken to further elaborate the 5-halothiazoles to pharmacologically interesting compounds.1. Campeau, L.-C. et al; J. Am. Chem. Soc. 2009, 131, 3291-3306. 2. Campeau, L.-C. et al; J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the Belgian Fonds National pour la Recherche Scientifique (FNRS) and the Walloon Region (BioWin project CANTOL: Convention n° 5678).
Original languageEnglish
PagesBook of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74
Number of pages1
Publication statusPublished - 1 Jul 2012
EventBalticum Organicum Syntheticum 2012 - Tallinn, Estonia
Duration: 1 Jul 20124 Jul 2012

Conference

ConferenceBalticum Organicum Syntheticum 2012
CountryEstonia
CityTallinn
Period1/07/124/07/12

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  • Projects

    CANTOL: Design and synthesis of indolamine dioxygenase (IDO) for the treatment of cancer

    MASEREEL, B., WOUTERS, J., Dolušić, E., FREDERICK, R., POUYEZ, J., Van den Eynde, B. J., Frère, J., Moser, M., Jean-Marie, B., Combalbert, J. & Stephenne, J.

    1/04/0831/03/12

    Project: Research

    Equipment

  • Activities

    • 2 Participation in conference

    Balticum Organicum Syntheticum 2012

    Eduard Dolusic (Poster)

    1 Jul 2012

    Activity: Participating in or organising an event typesParticipation in conference

    15th SIGMA-ALDRICH Organic Synthesis Meeting

    Eduard Dolusic (Poster)

    1 Dec 20112 Dec 2011

    Activity: Participating in or organising an event typesParticipation in conference

    Cite this

    Dolusic, E., Modaffari, S., Pochet, L., Wouters, J., Masereel, B., & Frédérick, R. (2012). Convenient one-pot formation of highly functionalized 5-halothiazoles. Book of Abstracts, Balticum Organicum Syntheticum, July 1-4 2012, Tallinn, Estonia, PO27, p. 74. Poster session presented at Balticum Organicum Syntheticum 2012, Tallinn, Estonia.