A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.

Research output: Contribution to conferencePoster

69 Downloads (Pure)

Abstract

A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES Eduard Dolusic, Sara Modaffari, Johan Wouters, Bernard Masereel and Raphaël Frédérick NAmur MEDIcine Center (NAMEDIC), NARILIS, 61 rue de Bruxelles, 5000 Namur, Belgium In the framework of our research program, we were interested in the synthesis of substituted thiazole N-oxides. However, treatment of starting thiazoles with mCPBA1 did not afford the desired 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, hydrobromide salts. Oxidative bromination mediated by mCPBA then occurred in the 5-position of the thiazole ring. Various 5-bromo-1,3-thiazoles bearing alkyl and aryl substituents (containing both electron withdrawing and electron donating groups) in the 2- and 4-positions very easily prepared in this way. These products formed rapidly, in an one-pot operation from simple starting materials, using mild conditions (room temperature) and avoiding the use of catalysts or hazardous reagents like elemental bromine. This convenient procedure allows simple and quick access to a range of highly functionalized thiazoles, which can be further elaborated by known chemical methods. References: 1. e. g. Campeau, L.-C, et al, J. Am. Chem. Soc. 2009, 131, 3291-3306 ; Campeau, L.-C, et al, J. Am. Chem. Soc. 2008, 130, 3276-3277. This work is supported by the FNRS and the Walloon Region (BioWin project CANTOL: Convention n° 5678).
Original languageEnglish
PagesBook of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25
Number of pages1
Publication statusPublished - 2011
Event15th SIGMA-ALDRICH Organic Synthesis Meeting - Spa, Belgium
Duration: 1 Dec 2011 → …

Conference

Conference15th SIGMA-ALDRICH Organic Synthesis Meeting
CountryBelgium
CitySpa
Period1/12/11 → …

Fingerprint Dive into the research topics of 'A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.'. Together they form a unique fingerprint.

  • 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., 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., Wouters, J., Masereel, B., & Frédérick, R. (2011). A CONVENIENT FORMATION OF HIGHLY FUNCTIONALIZED 5-BROMO-1,3-THIAZOLES.. Book of Abstracts, 15th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium, 1-2 December 2011, p. 25. Poster session presented at 15th SIGMA-ALDRICH Organic Synthesis Meeting, Spa, Belgium.